Triphenylphosphine → (4R)-4,5-Dihydro-2-(3-iodophenyl)-4-phenyloxazole

Participants

Reaction Steps

To a mixture of (+)-2-(3-iodobenzamido)-2(R)-phenylethan-1-ol (14.70 g, 40 mmol) and triphenylphosphine (13.64 g, 52 mmol) in dry tetrahydrofuran (350 ml) was added dropwise a solution of diethyl azodicarboxylate (10.52 g, 52 mmol) in dry tetrahydrofuran (15 ml). The reaction mixture was stirred for 18 h and volatiles removed by evaporation. The residue was purified by column chromatography on silica gel eluting with ethyl acetate-hexane (1:8) to afford (+)-4,5-dihydro-2-(3-iodophenyl)-4(R)-phenyloxazole (7.81 g, 56%) as a liquid.

Provenance & Evidence