Dimethylformamide → 3-Cyanocinnamyl alcohol

Participants

Reaction Steps

Dimethylformamide (0.1 ml) was added to a stirred suspension of 3-cyano-cinnamic acid (30 g) in dry ether (500 ml) containing oxalyl chloride (15 ml). The mixture was stirred for 6 hours, filtered and evaporated to give the crude acid chloride as a pale solid. A solution of this acid chloride in ether (100 ml) and tetrahydrofuran (100 ml) was added to a stirred suspension of sodium borohydride-doped alumina (20 g sodium borohydride on 200 g alumina) in ether (200 ml). The mixture was stirred for 1 hour and then filtered. The filtrate was evaporated and the residue was chromatographed on silica-gel eluting with 2:1 ether:hexane to give the product as a pale oil.

Provenance & Evidence