Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 2-[3-(3-bromophenyl)cyclobutylidene]acetate

Participants

Reaction Steps

3-(3-Bromo-phenyl)-cyclobutanone (2.03 g 9.02 mmol) and Triphenyl-phosphoranylidene acetic acid ethyl ester (15.72 gms 45.12 mmol) were dissolved in dichloromethane (30 mL) inside a CEM 80 ml microwave vessel. The solution was irradiated in a CEM Discover™ microwave instrument for 30 minutes at 120° C. Pressure reached a maximum of 180 PSI. The product was purified by column chromatography (isocratic; 10% diethyl ether in hexanes) to give 2.37 gm of an oil (89%) 1H NMR (400 MHz, DMSO-d6) δ ppm 1.20 (t, J=7.1 Hz, 3H) 2.89-3.00 (m, 1H) 3.03-3.11 (m, 1H) 3.16-3.27 (m, 1H) 3.46-3.57 (m, 1H) 3.63 (q, J=8.0 Hz, 1H) 4.08 (q, J=7.0 Hz, 2H) 5.71 (q, J=2.9 Hz, 1H) 7.25-7.35 (m, 2H) 7.39-7.43 (m, 1H) 7.48-7.52 (m, 1H); MS (APPI) m/z 295 [M+H]·+.

Provenance & Evidence