Triethylamine → 2-(Tetrahydro-2H-pyran-3-yl)ethyl methanesulfonate

Participants

Reaction Steps

A solution of 2-(tetrahydro-2H-pyran-3-yl)ethanol (1.54 gm) and triethylamine (3.3 ml) in dichloromethane (25 ml) was cooled (ice bath) and methanesulphonyl chloride (1.19 ml) added dropwise with stirring over 5 min. The reaction slowly warmed to ambient temperature as the ice bath melted. After 16 h the mixture was washed with saturated aq. sodium hydrogen carbonate, the aqueous layer extracted twice with dichloromethane and the combined extracts washed with dilute brine, dried by passing through a hydrophobic frit and evaporated to give the title compound as a brown oil, yield 2.38 g.

Provenance & Evidence