Ethyl Acetate → (E)-3-(7-Chloro-benzofuran-4-yl)-acrylonitrile

Participants

Reaction Steps

A solution of diethyl cyanomethylphosphonate (7.34 g) in dry tetrahydrofuran (20 ml) was added to a suspension of sodium hydride (60% oil dispersion; 1.65 g) in THF (40 ml) over 5 mins with ice cooling. After 15 min, a solution of 7-chloro-benzofuran-4-carbaldehyde in THF (20 ml) was added and after 5 mins the solution was warmed up and stirred at room temperature for 2 h. Brine (40 ml) and ethyl acetate (40 ml) were added, the phases separated and the aqueous extracted with ethyl acetate (2×20 ml). The extracts were dried (MgSO4) and evaporated and the residue crystallised from ethanol to give off-white fluffy needles (2.95 g) of (E)-3-(7-Chloro-benzofuran-4-yl)-acrylonitrile.

Provenance & Evidence