Dichloromethane → Methyl 2-methanesulfonyloxy-3-phenyl-propionate

Participants

Reaction Steps

A dichloromethane solution of methyl 2-hydroxy-3-phenylpropionate (33) is treated with triethylamine (1.1 equiv) and methanesulfonyl chloride (1.1 equiv) at 0° C. Upon completion of reaction, the mixture is dissolved in dichloromethane/ether and washed with saturated aqueous solution of sodium chloride, dried and concentrated. Purification of crude material by flash column chromatography (40% ethyl acetate in hexane) gives methyl 2-methanesulfonyloxy-3-phenylpropionate (1.6 g, 93%). 1H NMR (300 MHz CDCl3): δ 7.358-7.233 (m, 5H), 5.173 (dd, 4.26 Hz, 8.8 Hz, 1H), 3.793 (s, 3H), 3.301 (dd, 4.23 Hz, 14.38 Hz, 1H), 3.1295 (dd, 8.8 Hz, 14.3 Hz, 1H), 2.766 (s, 3H).

Provenance & Evidence