Category: 24621-61-2

A common heterocyclic compound, 24621-61-2,(S)-Butane-1,3-diol, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 24621-61-2

Example 25 (4-{(R)-3-[(2-CHLORO-3-TRIFLUOROMETHYL-BENZYL)-2, 2-DIPHENYLETHYL-AMINO]-BUTOXY}-INDOL-1- YL) acetic acid hydrochloride salt a) Toluene-4-sulfonic acid (S)-3-hydroxy-butyl ester To a solution of (S)-1, 3-butanediol (2.0 g, 22.0 MMOL) and Et3N (4.6 mL, 33.0 MMOL) in CH2CI2 (20 mL) at-20 C was added p-toluenesulfonyl chloride (4.46 g, 23.0 MMOL) and the reaction mixture was then warmed to RT and stirred overnight. The reaction mixture was washed with H20 and brine, dried over NA2SO4, filtered, and concentrated to give the title compound as a yellow oil (5.2 G, 96%)a) Toluene-4-sulfonic acid (S)-3-hydroxy-butyl ester To a solution of (S)-1, 3-butanediol (2.0 G, 22.0 MMOL) and Et3N (4.6 mL, 33.0 MMOL) in CH2CI2 (20 mL) at-20 C was added p-toluenesulfonyl chloride (4.46 g, 23.0 MMOL) and the reaction mixture was then warmed to RT and stirred overnight. The reaction mixture was washed with H20 and brine, dried over NA2SO4, filtered, and concentrated to give the title compound as a yellow oil (5.2 G, 96%), 24621-61-2

The chemical industry reduces the impact on the environment during synthesis, 24621-61-2,(S)-Butane-1,3-diol,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/23196; (2005); A2;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

24621-61-2,A common heterocyclic compound, 24621-61-2,(S)-Butane-1,3-diol, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

(Example 5-1) Under ice cooling, to a dichloromethane solution (20.0 ml) of (S)-1,3-butanediol (519 mg) were added triethylamine (1.04 ml) and tert-butylchlorodiphenylsilane (1.63 ml), followed by stirring at room temperature overnight. The reaction solution was poured into a saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography to afford (2S)-4-{[tert-butyl(diphenyl)silyl]oxy}butan-2-ol (1.69 g). 1H NMR(400 MHz,CDCl3) delta: 1.05 (9H, s), 1.22 (3H, d, J = 6.3 Hz), 1.58-1.68 (1H, m), 1.69-1.81 (1H, m), 3.31 (1H, d, J = 2.0 Hz), 3.80-3.91 (2H, m), 4.07-4.15 (1H, m), 7.37-7.50 (6H, m), 7.69 (4H, d, J = 6.2 Hz).

The chemical industry reduces the impact on the environment during synthesis, 24621-61-2,(S)-Butane-1,3-diol,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; Daiichi Sankyo Company, Limited; EP2471792; (2012); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials.24621-61-2,A new synthetic method of this compound is introduced below.24621-61-2

(S)-(+)-Butane-1 ,3-diol (3.00 mmol, 0.270 g) was added to a stirred solution of imidazole (5.99 mmol, 0.41 g) and tert-butyldimethylsilyl chloride (3.00 mmol, 0.45 g) at room temperature. After six hours at room temperature water (50 mL) was added and extracted twice with dichloromethane (20 mL). The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated in vacuo to yield (S)-4- (tert-butyldimethylsilyloxy)butan-2-ol (0.654 g).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, (S)-Butane-1,3-diol.

Reference£º
Patent; N.V. ORGANON; MAN de,, Adrianus Petrus Antonius; REWINKEL,, Johannes Bernardus Maria; JANS,, Christiaan Gerardus Johannes Maria; RAAIJMAKERS,, Hans Cornelis Andreas; WIJKMANS,, Jacobus Cornelis Henricus Maria; WO2011/95556; (2011); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

A common heterocyclic compound, 24621-61-2,(S)-Butane-1,3-diol, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 24621-61-2

To a stirring solution of (S)-1, 3-butanediol (1.0 g, 0.01 MMOL) and triethylamine (1.39 g, 0.014 MMOL) in dichloromethane (10 mL) at-20C was added dropwise p- toluenesulfonyl chloride and the mixture was stirred for 2 h. The reaction mixture was then warmed to RT and stirred overnight. The reaction mixture was poured into cold H20 (20 mL), and extracted three times with DICHLOROMETHANE. The organic extracts were then washed with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to give 2.6 g (96% yield) of title compound as an oil. MS (ESI) 244.8 (M+). The crude tosylat was used without further purification.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,(S)-Butane-1,3-diol,24621-61-2,its application will become more common.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/43939; (2004); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials.24621-61-2,A new synthetic method of this compound is introduced below.24621-61-2

To a solution of (S)-1,3-butanediol (807 mg) in DMF (10 mL) at 0C was added potassium t-butoxide (7.2 mL of a 1M solution in THF). After 1 h, the mixture was cooled to -20C and then 2-chloro-3-(4-methylsulfonyl)phenyl-5-trifluoromethylpyridine (1 g) was added as a solid. The resulting mixture was stirred for 24 h, warming to r.t. To the mixture was added saturated NH4Cl and the mixture was extracted with ethyl acetate. The organics were dried (MgSO4) and concentrated. Flash chromatography (1:1 hexane/ethyl acetate) provided the title compound as a white solid (323 mg).1H NMR (300 MHz, acetone-d6): d 1.15 (d, 3H), 1.75-2.00 (m, 2H), 3.15 (s, 3H), 3.65 (d, 1H), 3.85-4.00 (m, 1H), 4.60 (dd, 2H), 7.95 (d, 2H), 8.03 (d, 2H), 8.10 (d, 1H), 8.57 (d, 1H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, (S)-Butane-1,3-diol.

Reference£º
Patent; MERCK FROSST CANADA & CO.; EP1012142; (2004); B1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact.24621-61-2,(S)-Butane-1,3-diol, it is a common compound, a new synthetic route is introduced below.24621-61-2

Example 4 Synthesis of Maytansinoid 4k,l (d) S-1,3-Di-O-p-toluenesulfonyl-butane 22: A solution of S-(-)-1,3-butanediol (21, 2.00 g (22.22 mmol) in a mixture of dry pyridine (40 mL) and dry toluene (60 mL) was treated with p-toluenesulfonyl chloride (12.70 g, 66.84 mmol) under argon at 0 C. After stirring at 0 C. for 5 min. followed by stirring at room temperature for 2 h, the mixture was evaporated under vacuum. The residue was redissolved in ethyl acetate, washed with 0.1 M aqueous NaHCO3, and saturated NaCl. The organic layer was separated, dried over MgSO4, filtered and evaporated. The residue was purified by chromatography over silica gel, eluding with 1:2 ethyl acetate/hexane to give 6.25 g (71%) of the title product 22 Rf=0.40 (1:1 EtOAc/hexane); 1H NMR (CDCl3) 7.76 (dd, 4H, J=1.0, 8.0 Hz), 7.35 (dt, 4H, J=0.4, 8.0+8.0 Hz), 4.70 (m, 1H), 4.03 (m, 1H), 3.94 (m, 1H), 2.46 (s, 6H), 1.92 (m, 2H), 1.26 (d, 3H, J=6.3 Hz); 13C NMR 145.17, 133.00, 130.11, 128.12, 127.91, 76.28, 66.21, 36.08, 21.86, 21.06; MS: 420.99 (M+Na)+., 24621-61-2

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 24621-61-2, other downstream synthetic routes, hurry up and to see.

Reference£º
Patent; IMMUNOGEN, INC.; US2004/235840; (2004); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. (S)-Butane-1,3-diol,24621-61-2, This compound has unique chemical properties. The synthetic route is as follows.,24621-61-2

Preparation of (3S)-1-p-Toluenesulfonyloxy-3-triethylsilyloxy-butane (2b); To a stirred, solution of the(S)-(+)-1,3-butanediol 1b (1 g, 11.1 mmol), DMAP (30 mg, 0.25 mmol) and Et3N (4.6 mL, 3.33 g, 33 mmol) in anhydrous methylene chloride (20 mL) p-toluenesulfonyl chloride (2.54 g, 13.3 mmol) was added at 0 C. The reaction mixture was stirred at 4 C. for 22 h. Methylene chloride was added and the mixture was washed with water, dried (Na2SO4) and concentrated under reduced pressure. A residue was chromatographed on silica gel with hexane/ethyl acetate (8:2, then 1:1) to afford the tosylate (2.31 g, 85% yield) as a colorless oil.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 24621-61-2.

Reference£º
Patent; WISCONSIN ALUMNI RESEARCH FOUNDATION; US2012/283228; (2012); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 24621-61-2,(S)-Butane-1,3-diol, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.24621-61-2

To a solution of (S)+}1,3-butanediol (10.0 g, 0.110 mol), was added triphenylmethylchloride (33.0 g, 0.330 mol), 4-dimethylaminopyridine (1.40 g, 11.5 mmol) in CH2Cl/pyridine (1:1, 500 mL).Stirring was continued over 48 h. The solvent was removed, the mixture was diluted with ether, washed with brine and dried over Na2SO4. The organic solution was filtered and concentrated. Silica gel chromatography with (5% ethyl acetate/hexanes) produced a clear oil (24 g) in 70% yield., 24621-61-2

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, (S)-Butane-1,3-diol.

Reference£º
Patent; Bristol-Myers Squibb Company; Merck & Co. Inc.; US6967196; (2005); B1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 24621-61-2,(S)-Butane-1,3-diol, as follows.24621-61-2

Example 4 Synthesis of Maytansinoid 4k,l (d) S-1,3-Di-O-p-toluenesulfonyl-butane 22: A solution of S-(-)-1,3-butanediol (21, 2.00 g (22.22 mmol) in a mixture of dry pyridine (40 mL) and dry toluene (60 mL) was treated with p-toluenesulfonyl chloride (12.70 g, 66.84 mmol) under argon at 0 C. After stirring at 0 C. for 5 min. followed by stirring at room temperature for 2 h, the mixture was evaporated under vacuum. The residue was redissolved in ethyl acetate, washed with 0.1 M aqueous NaHCO3, and saturated NaCl. The organic layer was separated, dried over MgSO4, filtered and evaporated. The residue was purified by chromatography over silica gel, eluding with 1:2 ethyl acetate/hexane to give 6.25 g (71%) of the title product 22 Rf=0.40 (1:1 EtOAc/hexane); 1H NMR (CDCl3) 7.76 (dd, 4H, J=1.0, 8.0 Hz), 7.35 (dt, 4H, J=0.4, 8.0+8.0 Hz), 4.70 (m, 1H), 4.03 (m, 1H), 3.94 (m, 1H), 2.46 (s, 6H), 1.92 (m, 2H), 1.26 (d, 3H, J=6.3 Hz); 13C NMR 145.17, 133.00, 130.11, 128.12, 127.91, 76.28, 66.21, 36.08, 21.86, 21.06; MS: 420.99 (M+Na)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 24621-61-2, and friends who are interested can also refer to it.

Reference£º
Patent; IMMUNOGEN, INC.; US2004/235840; (2004); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 24621-61-2,(S)-Butane-1,3-diol, as follows.24621-61-2

EXAMPLE INEL SynthesisPreparation of (3S)-1-p-Toluenesulfonyloxy-3-triethylsilyloxy-butane (2); To a stirred solution of the (S)-(+)-1,3-butanediol 1 (1 g, 11.1 mmol), DMAP (30 mg, 0.25 mmol) and Et3N (4.6 mL, 3.33 g, 33 mmol) in anhydrous methylene chloride (20 mL)p-toluenesulfonyl chloride (2.54 g, 13.3 mmol) was added at 0 C. The reaction mixture was stirred at 4 C. for 22 h. Methylene chloride was added and the mixture was washed with water, dried (Na2SO4) and concentrated under reduced pressure. A residue was chromatographed on silica gel with hexane/ethyl acetate (8:2, then 1:1) to afford the tosylate (2.31 g, 85% yield) as colorless oil.To a stirred solution of the tosylate (2.31 g, 9.5 mmol) and 2,6-lutidine (1.2 mL, 1.12 g, 10.5 mmol) in anhydrous methylene chloride (15 mL) triethylsilyl trifluoromethanesulfonate (2.1 mL, 2.51 g, 9.5 mmol) was added at -50 C. The reaction mixture was allowed to warm to room temperature (4 h) and stirring was continued for additional 20 h. Methylene chloride was added and the mixture was washed with water, dried (Na2SO4) and concentrated under reduced pressure. A residue was chromatographed on silica gel with hexane/ethyl acetate (97:3) to afford the product 2 (2.71 g, 80% yield) as a colorless oil:[alpha]D+18.0 (c 2.38, CHCl3); 1H NMR (400 MHz, CDCl3) delta7.77 (2H, d, J=8.2 Hz, o-HTs), 7.33 (2H, d, J=8.2 Hz, m-HTs), 4.10 (2H, t, J=6.1 Hz, 1-H2), 3.90 (1H, m, 3-H), 2.43 (3H, s, McTs), 1.72 (2H, m, 2-H2), 1.10 (3H, d, J=6.2 Hz, 4-H3), 0.88 (9H, t, J=8.0 Hz, 3¡ÁSiCH2CH3), 0.50 (6H, q, J=8.0 Hz, 3¡ÁSiCH2CH3); 13C NMR (100 MHz) delta 144.62 (s, p-CTs), 133.03 (s, i-CTs), 129.72 (d, m-CTs), 127.82 (d, o-CTs), 67.78 (t, C-1), 64.46 (d, C-3), 38.47 (t, C-2), 23.82 (q, C-4), 21.52 (q, MeTs), 6.71 (q, SiCH2CH3), 4.77 (t, SiCH2CH3); MS (EI) m/z 359 (5, MH+), 329 (87, M+ -C2H5), 259 (100), 233 (54), 197 (50), 179 (74), 163 (40), 149 (48), 135 (38), 115 (53), 91 (71); exact mass calculated for C15H25O4SSi (M+ -C2H5) 329.1243, found 329.1239.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (S)-Butane-1,3-diol, and friends who are interested can also refer to it.

Reference£º
Patent; WISCONSIN ALUMNI RESEARCH FOUNDATION; US2007/191316; (2007); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate