Tributylphosphine → 3-{4-[3,3-Bis-(4-bromo-phenyl)-allyloxy]-phenyl}-propionic Acid Ethyl Ester

Participants

Reaction Steps

Under a atmosphere of nitrogen, azodicarboxylic dipiperidide (504 mg, 2.0 mmol) was added at 0-5° C. to a stirred solution of tributylphosphine (404 mg, 2.0 mmol), 3-(4-hydroxy-phenyl)-propionic acid ethyl ester (388 mg, 2.0 mmol) and 3,3-bis-(4-bromophenyl)prop-2-en-1-ol (736 mg, 2.0 mmol) in dry THF (50 ml), the mixture warmed to room temperature, and stirred for 4 h. The reaction mixture was concentrated in vacuo, and added water and ethyl acetate (75 ml each). The aqueous layer was collected and further extracted with ethyl acetate (2×75 ml). The organic layers were combined, washed with water, dried (MgSO4) and evaporated. The crude product was then purified by column chromatography on silica (25% ethylacetane in heptane eluent) to give 1.0 g (92%) of the title compound.

Provenance & Evidence