Triphenylphosphine → HCID 19744806, compound

Participants

Reaction Steps

100 mg of 4-(3-thienyl)-2-thiophenecarboxaldehyde and 250 mg of 3-chloromethylbenzyltriphenylphosphonium chloride [prepared by refluxing a xylene solution of α,α'-dichloro-m-xylene and triphenylphosphine] were suspended in 1 ml of tetrahydrofuran, and 31 mg of 60% oily sodium hydride was added under ice cooling. The mixture was stirred for 1.5 hours at room temperature, and the solvent was evaporated. The residue was neutralized with 1 N HCl, and extracted with ethyl acetate. The extract was worked up in a customary manner, purified by silica gel column chromatography [Wakogel C-300, 5 g; eluting solvent: hexane/ethyl acetate=10/1], and recrystallized from chloroform-hexane to give 80 mg (yield 49%) of the captioned compound as a pale yellow crystalline powder, m.p. 137°-138° C.

Provenance & Evidence