Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 86638801, compound

Participants

Reaction Steps

±(1S,5R,6S)-3-chloro-6-phenethylbicyclo[3.1.0]hex-2-ene-2-carbaldehyde (11 mmol crude weight) was olefinated with ethoxycarbonylmethylene triphenylphosphorane (4.6 g, 13.2 mmol) according to General Procedure 1.1.B to afford the title compound. The material was purified by chromatography, eluting with heptane-EtOAc, gradient 0 to 10% EtOAc. 2.2 g. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.08-1.19 (m, 1H), 1.23-1.31 (m, 1H), 1.30-1.37 (m, 3H), 1.39-1.51 (m, 1H), 1.59-1.68 (m, 1H), 2.14 (td, J=7.25, 3.03 Hz, 1H), 2.38 (dd, J=19.57, 2.68 Hz, 1H), 2.53-2.66 (m, 2H), 2.92 (dd, J=19.55, 7.88 Hz, 1H), 4.20-4.31 (m, 2H), 6.04 (d, J=15.72 Hz, 1H), 7.10-7.22 (m, 3H), 7.23-7.31 (m, 2H), 7.61 (d, J=15.72 Hz, 1H).

Provenance & Evidence