Triphenylphosphine → 2-(3-benzyloxyphenyl)-4,5-dihydro-4(R)-phenyloxazole

Participants

Reaction Steps

To a mixture of 2-(3-benzyloxybenzamido)-2(R)-phenylethan-1-ol (29 g, 83 mmol) and triphenylphosphine (28.4 g, 108 mmol) in dry tetrahydrofuran (200 ml) was added dropwise a solution of diisopropyl azodicarboxylate (19.6 ml, 108 mmol) in dry tetrahydrofuran (30 ml). The reaction mixture was stirred for 4 hours and volatiles removed by evaporation. The residue was purified by column chromatography on silica gel eluting with ethyl acetate-hexane (=1:9) to afford 2-(3-benzyloxyphenyl)-4,5-dihydro-4(R)-phenyloxazole (23.5 g, 85%) as pale yellow solids.

Provenance & Evidence