Category: 24621-61-2

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.

Step E (2-TOLUENE-4-SULFONIC acid 3-hydroxy-butyl ester; A solution of (S)- (+)-1, 3-butanediol (9.5 g, 0.105 mol) and Et3N (12.8 g, 0.126 mol) in CH2C12 (200 mL) is treated with dibutyltin oxide (0.52 g, 2.08 mmol) and THENP-TOLUENESULFONYL chloride (20.09 g, 0.105 mol) is added as a solid in portions over 30 minutes at rt. The resultant mixture is stirred at rt for 17 hours under N2. The reaction is quenched with 1 N HC1 (50 mL), diluted with water and extracted with EtOAc. The organic layer is dried (NA2SO4), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 98/2 CH2C12/ACN (to elute the unreactedp-toluenesulfonyl chloride) and then 2/1 hexanes/acetone to afford 18. 67 g (73%) the title compound. Rf== 0.23, Rf bis-tosylate = 0.53 (98/2 CH2C12/ACN).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand 24621-61-2 reaction routes.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2005/19151; (2005); 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 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

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).

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; 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

24621-61-2,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.

Representative example 44: Synthesis of 1-((R)-3-(2-(4-hydroxy-1-((2R,3S)-2- propyl-1-(3-(trifluoromethyl)picolinoyl)-3-(5-(trifluoromethyl)thiophen-3- yloxy)piperidine-3-carbonyl)piperidin-4-yl)phenoxy)butyl)cyclobutanecarboxylic acid A31. Step 1: To a 0C DCM (100 mL) solution of (S)-(+)-1 ,3-Butanol (7g, 77.6 mmol) containing Et^N (14 mL, 1.3equiv) was added drop wise a DCM solution (60 mL) of TsCI (1.05 equiv, 15g). Reaction was warmed-up to Rt and stirred overnight. After 18 hours, the DCM layer was washed with HCI 1.0N (X2), then NaHC03, then brine. Organic layer was dried over MgS04, filtered and concentrated down to 15 g of crude oil. The residue was purified by silica gel chromatography (10% to 40% EtOAc in hexanes) to provide 13 g (69% yield) of (S)-3-hydroxybutyl 4- methylbenzenesulfonate 94.

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; SCHERING CORPORATION; BOGEN, Stephane, L.; MA, Yao; WANG, Yaolin; LAHUE, Brian Robert; NAIR, Latha, G.; SHIZUKA, Manami; VOSS, Matthew Ernst; KIROVA-SNOVER, Margarita; PAN, Weidong; TIAN, Yuan; KULKARNI, Bheemashankar, A.; GIBEAU, Craig, R.; LIU, Yuan; SCAPIN, Giovanna; RINDGEN, Diane; DOLL, Ronald, J.; GUZI, Timothy, J.; HICKLIN, Danny, J.; NOMEIR, Amin; SEIDEL-DUGAN, Cynthia; SHIPPS, Gerald, W., Jr.; MACCOSS, Malcolm; WO2011/46771; (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

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 1; Preparation 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 a colorless oil.

According to the analysis of related databases, (S)-Butane-1,3-diol, the application of this compound in the production field has become more and more popular.

Reference£º
Patent; DeLuca, Hector F.; Clagett-Dame, Margaret; Plum, Lori A.; Chiellini, Grazia; Grzywacz, Pawel; US2008/81800; (2008); 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 1; Preparation 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 a colorless oil., 24621-61-2

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. 24621-61-2, We look forward to the emergence of more reaction modes in the future.

Reference£º
Patent; DeLuca, Hector F.; Clagett-Dame, Margaret; Plum, Lori A.; Chiellini, Grazia; Grzywacz, Pawel; US2008/81800; (2008); 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

p-Toluenesulfonyl chloride (381 mg, 1 .68 mmol) was dissolved in anhydrous DCM (10 mL) at RT under N2. (s)-(+)-1 ,3-butandiol (300 muIota_, 3.33 mmol) was added followed by NEt3 (450 muIota_, 3.33 mmol) and the solution stirred for 18 h. The solution was partitioned with H2O (15 mL) and extracted with DCM (3 x 10 mL), Combined organic fractions were dried by phase separator and the mixture loaded onto silica for purification by flash chromatography. The desired compound A32 was isolated as a clear oil (144 mg, 29%); -NMR (400 MHz, DMSO-c/6): delta 7.78 (d, J = 8.0 Hz, 2H), 7.48 (d, J = 8.0 Hz, 2H), 4.56 (d, J = 5.0 Hz, 1 H), 4.12-4.00 (m, 2H), 3.65-3.57 (m, 1 H). 2.43 (s, 3H), 1 .69-1 .54 (m, 2H), 1 .00 (d, J = 6.0 Hz, 3H).

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; IMPERIAL INNOVATIONS LIMITED; SCHNEIDER, Michael; NEWTON, Gary; CHAPMAN, Katie; PERRIOR, Trevor; JARVIS, Ashley; LOW, Caroline; AQIL, Rehan; FISHER, Martin; BAYFORD, Melanie; CHAPMAN, Nicholas; MARTIN, Nicholas; REISINGER, Tifelle; NEGOITA-GIRAS, Gabriel; (260 pag.)WO2019/73253; (2019); 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

24621-61-2,The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a downstream synthesis route of the compound 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., 24621-61-2

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; 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

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 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).

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; 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

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

The flask was charged with (S) -butane-1,3-diol (1.00 g, 11.10 mmol) in dichloromethane (DCM) (27 mL),Triethylamine (1.347 g, 13.32 mmol),4-Dimethylaminopyridine (0.136 g, 1.110 mmol) and 4-methylbenzene-1-sulfonyl chloride (2.327 g, 12.21 mmol) were added. The reaction was stirred at room temperature for 1 hour.Quench the reaction with saturated NH 4 Cl,Extracted with DCM. The organic portion was dried over MgSO 4, filtered and concentrated under reduced pressure to give a residue which was purified by silica gel chromatography eluting with 0-50% ethyl acetate / heptane to give the product (0. 288 g, 1.179 mmol, yield 10.62%).

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; Abbvie Incorporated; Argiriadi, Maria A.; Breinlinger, Eric C.; Chien, Ellen Yulin Tsai; Cowart, Marlon D.; Frank, Kristine E.; Friedman, Michael M.; Hardy, David J.; Herold, J. Martin; Liu, Huaqing; Chu, Wei; Scanio, Marc J.; Schrimpf, Michael R.; Vargo, Thomas R.; Van Epps, Stacy A.; Webster, Matthew P.; Little, Andrew J.; Dunstan, Teresa A.; Katcher, Matthew H.; Schedler, David A.; (232 pag.)JP6557436; (2019); 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

Triethylamine (1.173 g) is added dropwise to a solution of 2.246 g triisopropylchlorosilane and 1 g (S)-(+)-1,3-butanediol in 15 ml of dry tetrahydrofuran. The mixture is stirred for 48 hours at room temperature, then is diluted with 400 ml of tert-butyl methyl ether and washed respectively with 30 ml 1N HCl, 50 ml water and 50 ml of brine. The organic phase is dried (sodium sulphate), filtered and evaporated to dryness. The residue is purified by means of flash column chromatography (SiO2 60F) to provide the title compound as a colorless oil. Rf=0.31 (EtOAc-heptane 1:5).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. 24621-61-2, We look forward to the emergence of more reaction modes in the future.

Reference£º
Patent; Herold, Peter; Mah, Robert; Stutz, Stefan; Tschinke, Vincenzo; Schumacher, Christoph; Stojanovic, Aleksandar; Jotterand, Nathalie; Behnke, Dirk; US2007/167433; (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