Triethylamine → 2-[(2-Methylpropan-2-yl)oxy]ethyl methanesulfonate

Participants

Reaction Steps

Combine 2-t-butoxyethanol (3.37 g, 28.5 mmol), triethylamine (6 mL, 43 mmol), and dichloromethane (150 mL). Cool in an ice bath. Add dropwise methanesulfonyl chloride (2.9 mL, 37.5 mmol). After 3 days, dilute the reaction mixture with dichloromethane and extract with a saturated solution of sodium bicarbonate and then brine. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give 2-(t-butoxy)ethyl mesylate: Rf=0.75 (silica gel, 50% ethyl acetate/hexane).

Provenance & Evidence