tert-Butyl (triphenylphosphoranylidene) acetate → (E)t-Butyl 7-phenyl-2-heptenoate

Participants

Reaction Steps

A stirred solution of 5-phenylpentanal (9.96 g, Reference Example 6) in anhydrous tetrahydrofuran (100 ml) at room temperature was treated with (tert-butoxycarbonylmethylene)triphenylphosphorane (27.5 g). The resulting orange solution was stirred for 2.5 hours then evaporated. The residual crude product was subjected to flash chromatography on silica eluting with a mixture of hexane and ethyl acetate (19:1, v/v) to afford the title compound (12.4 g) as a colourless oil. NMR (CDCl3): δ1.45 (s,9H), 1.65 (m,4H), 2.18 (q,2H), 2.61 (t,2H), 5.70 (d,1H), 6.82 (dt,1H), 7.10-7.30 (m,5H).

Provenance & Evidence