1,2-Dimethoxyethane → 2,2-Bis-(4-fluoro-phenyl)-4-hydroxy-butyronitrile

Participants

Reaction Steps

Ethylene glycol dimethyl ether (10 ml) was treated with sodium borohydride (142 mg) and LiCl (228 mg) and the mixture stirred for 30 min. 3-Cyano-3,3-bis-(4-fluoro-phenyl)-propionic acid ethyl ester (847 mg) was added and the mixture stirred for 6 hrs, before more sodium borohydride (36 mg) and LiCl (57 mg) were added and stirring continued overnight. The mixture was poured into water and extracted (3×) with ethyl ether. The combined organic extracts were dried over Na2SO4. Filtration, concentration and flash chromatography of the residue afforded the title compound (41%; Isolated as an oil).

Provenance & Evidence