Triethylamine → Methanesulfonic acid 1-naphthalen-1-yl-cyclopentylmethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of (1-naphthalen-1-yl-cyclopentyl)-methanol (340) (9.0 g, 39.8 mmol) in dichloromethane (180 mL) was added triethylamine (11.0 mL, 79.5 mL) and the reaction mixture was cooled to 0° C. To this reaction mixture was added mesylchloride and stirring was continued at room temperature for 18 h (silica TLC, 10% ethyl acetate in hexane; Rf=0.2). The reaction mass was diluted with dichloromethane (100 mL), washed with water (2×100 mL) and brine (100 mL) and dried and concentrated in vacuum to get a crude mass which was purified by Combi-Flash using gradient eluent mixture of ethyl acetate and hexane to get pure methanesulfonic acid 1-naphthalen-1-yl-cyclopentylmethyl ester (341) (4.25 g, 35%) as a white solid.

Provenance & Evidence