Hydrochloric Acid → HCID 15037028, compound
Reaction equation
[OH:1][C@H:2]([CH2:6][OH:7])[CH2:3][C:4]#[N:5].[S:8](Cl)([CH3:11])(=[O:10])=[O:9].Cl>N1C=CC=CC=1.C(Cl)Cl>[OH:1][C@H:2]([CH2:6][O:7][S:8]([CH3:11])(=[O:10])=[O:9])[CH2:3][C:4]#[N:5]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
(3S)-3,4-Dihydroxybutyronitrile (16.2 g, 160 mmol) was dissolved in pyridine (26.0 ml). To the resulting solution, a solution of mesyl chloride (14.8 ml) in methylene chloride (160 ml) was added at 0° C. and stirred at 0° C. for 6 hours. Then, the pH of the mixture was adjusted at 2 with 6N hydrochloric acid, and the mixture was extracted with methylene chloride. After the organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated off. The residue was purified with silica gel column chromatography (acetone:chloroform=5:95) to obtain (3S)-3-hydroxy-4-methanesulfonyloxybutyronitrile (15.2 g). Yield, 53 %.
Workup
- extractionthe mixture was extracted with methylene chloride
- dry with materialAfter the organic layer was dried over anhydrous sodium sulfate
- customthe solvent was evaporated off
- customThe residue was purified with silica gel column chromatography (acetone:chloroform=5:95)
Sources & evidence
- ORD record
- ord-308f09106e6a4cd49806c49f5c90e3cf
- Source dataset
- uspto-grants-1992_01
- Patent number
- US05079382
Reaction notes
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