Sodium hydride → (E)-3-(7-Fluoro-benzofuran-4-yl)-acrylonitrile

Participants

Reaction Steps

A solution of diethyl cyanomethylphosphonate (5.35 g) in dry ethylene glycol dimethyl ether (DME; 20 ml) was added to a suspension of sodium hydride (60% oil dispersion; 1.32 g) in DME (20 ml) at 0° under nitrogen over 5 mins. After 15 min, a solution 7-fluoro-benzofuran-4-carbaldehyde (4.51 g) in DME (20 ml) was added and after 5 mins the solution was warmed up and stirred at room temperature for 2 h. Ammonium chloride solution (200 ml) and ethyl acetate (150 ml) were added, the phases separated and the aqueous extracted with ethyl acetate (2×150 ml). The extracts were dried (MgSO4) and evaporated and the residue triturated under ether (20 ml) and filtered to give the E isomer as a buff coloured solid (3.07 g)

Provenance & Evidence