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

Participants

Reaction Steps

To a solution of 5-phenylpentanal (60 mmol) in anhydrous THF (100 mL) at room temperature is added (t-butoxycarbonylmethylene)triphenyl-phosphorane (27.5 g, 72 mmol). The resulting orange solution is stirred for 2.5 hours, after which TLC analysis indicated complete reaction. The reaction mixture is concentrated in vacuo to afford a crude product which is chromatographed on silica gel (hexane/EtOAc, 19:1) to afford 12.4 g of t-butyl 7-phenyl-2-heptenoate (80%) as a colorless oil. TLC [pet-ether/EtOAc, 9:1, Rf (aldehyde)=0.60, Rf (ester)=0.80]. 1H NMR (300 MHz, CDCl3) δ 1.45 (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) ppm.

Provenance & Evidence