Triethylamine → 1,4-Dioxaspiro(4.5)decan-8-yl methanesulfonate

Participants

Reaction Steps

A stirred solution of 14.2 grams (0.090 mole) of 1,4-dioxaspiro[4.5]decan-8-ol and 10.0 grams (0.099 mole) of triethylamine in 100 mL of methylene chloride is cooled to 0° C., and a solution of 7.7 mL (0.099 mole) of methanesulfonyl chloride in 25 mL of methylene chloride is added drop-wise at a rate to maintain the reaction mixture temperature at 0° C. to 5° C. Upon completion of addition, the reaction mixture is allowed to warm to ambient temperature. The reaction mixture is then washed with two 75 mL portions of an aqueous 5% sodium bicarbonate solution and then with 75 mL of an aqueous solution saturated with sodium chloride. The organic layer is dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, yielding 8-methylsulfonyloxy-1,4-dioxaspiro[4.5]decane

Provenance & Evidence