Citric Acid → trans-5-Tert-butoxycarbonyl-2-cyanomethyltetrahydrothiophene

Participants

Reaction Steps

To a stirred solution of trans-5-tert-butoxycarbonyl-2-chloromethyltetrahydrothiophene (3.5 g) in dimethylformamide (15 ml), sodium cyanide (1.5 g) is added and the mixture was stirred for 5 hours at 60°-70° C. 5% aqueous citric acid solution is added to the mixture and extracted with ethyl acetate - benzene (1:1). The organic layer is washed with water and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The oily residue is purified by a silica gel column chromatography to give trans-5-tert-butoxycarbonyl-2-cyanomethyltetrahydrothiophene.

Provenance & Evidence