Dimethylformamide → 3-(5-Cyano-2-thiophenyl)-2-propenol

Participants

Reaction Steps

Dimethylformamide (0.1 ml) was added to a stirred suspension of 3-(5-cyano-2-thiphenyl)-propenoic acid (3.7 g) in dry ether (100 ml) and dry tetrahydrofuran (100 ml) containing oxalyl chloride (2.2 ml). The mixture was stirred for 2 hours then the clear solution was decanted from a little dark tar and evaporated to give the crude acid chloride as a pale solid. A solution of this acid chloride in ether (50 ml) and tetrahydrofuran (50 ml) was added rapidly to a stirred suspension of sodium borohydride doped alumina (3.5 g sodium borohydride on 35 g alumina) in ether (100 ml) with cooling to keep at 15°-20° C. The mixture was stirred for 1 hour and then filtered. The filtrate was evaporated and the residue was chromatographed on silica-gel eluting with ether to give the product as a pale solid.

Provenance & Evidence