Triethylamine → (1-Phenylcyclopentyl)methyl methanesulfonate

Participants

Reaction Steps

To a stirred solution of (1-phenyl-cyclopentyl)-methanol] (278) (10 g, 56.73 mmol) in dichloromethane (110 mL) was added triethyl amine (16 mL, 113.47 mmol) followed by mesyl chloride (5.3 mL, 68.08 mmol) at 0° C. Stirring was continued at room temperature for 16 h. After completion of the reaction, the reaction mixture was diluted with dichloromethane (50 mL) and washed with water (100 mL) and saturated aqueous sodium bicarbonate solution (50 mL) and brine (50 mL). The separated organic fraction was dried and concentrated. The crude product was purified by Combi-Flash column (eluted at 10-20% ethyl acetate in hexane) to get methanesulfonic acid 1-phenyl-cyclopentylmethyl ester (279) (12 g, 83.16%) as a yellow semi-solid.

Provenance & Evidence