Hydrochloric Acid → HCID 20355557, compound

Participants

Reaction Steps

To a solution of 4-benzyloxy-3-hydroxy-1-butane-sulfonamide (1.6 g., 0.0062 mole) in pyridine (15 ml.), which is stirred and cooled in an ice bath, is added p-toluenesulfonyl chloride (1.18 g., 0.0062 mole). The reaction mixture is stirred at room temperature for 20 hours and then poured into water (100 ml.). This mixture is extracted with ethyl acetate-ether (1:1) (2 × 100 ml.). The organic phase is washed with brine, 3N hydrochloric acid, brine again, and then dried over sodium sulfate. Evaporation affords an oil that is dissolved in dimethylformamide (15 ml.); potassium carbonate (1.2 g.) is added, and the mixture is heated on the steam bath for 2.5 hours. Water is added to the cooled mixture, which is acidified (dilute HCl) and then extracted with ethyl acetate (2 × 75 ml.). The organic phase is washed with brine, dried over sodium sulfate, and concentrated in vacuo. The resulting oil is purified by chromatography over silica gel using ethyl acetate-hexane (60:40) to elute. From the proper fraction, there is obtained 1.2 g. (81%) of the title compound as a clear, viscous oil.

Provenance & Evidence