Sodium hydride → HCID 12661867, compound

Participants

Reaction Steps

A solution of diethyl cyanomethylphosphonate (11.5 ml) in dry ethylene glycol dimethyl ether (DME; 10 ml) was added dropwise to a suspension of sodium hydride (60%; 2.914 g) in DME (50 ml) at 0° under nitrogen. The mixture was stirred at 0° for 20 mins. Then a solution of 5-chloro-benzofuran-4-carbaldehyde mixture with 5-chloro-benzofuran-6-carbaldehyde (10.95 g) in DME (50 ml) was added in one portion. The mixture was heated at 60° for 2 h, cooled to room temperature and partitioned between water (150 ml) and ether (3×100 ml). The combined organic extracts were washed with brine (2×100 ml) and dried (MgSO4). The solvent was evaporated and the residue purified by column chromatography. Elution with cyclohexane/ethyl acetate 20:1 gave the title compound as a colourless solid (6.75 g)

Provenance & Evidence