Ethylene glycol monoallyl ether → Allyl methanesulfonylethyl ether

Participants

Reaction Steps

Combine allyl hydroxyethyl ether (1.02 g, 10 mmol), and diisopropylethylamine (4.0 mL, 23 mmol), and dichloromethane (20 mL). Cool in an ice-bath. Add dropwise, methanesulfonyl chloride (1.0 mL, 13 mmol). After 1.5 hours, extract the reaction mixture with 1 M aqueous hydrochloric acid solution, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution. Dry the organic layer over Na2SO4, filter, and evaporate invacuo to obtain allyl methanesulfonylethyl ether: Rf =0.80 (silica gel, 20% ethyl acetate/dichloromethane).

Provenance & Evidence