Methanol → (1RS,4SR,5RS)-4-(3-methanesulfonyloxypropyl)-4-methyl-1-vinyl-3,8-dioxabicyclo[3.2.1]octane

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Reaction Steps

Methanesulfonyl chloride (200 mg, 2.6 mM) is added slowly to a mixture of (1RS,4SR,5RS)-4-(3-hydroxypropyl)-4-methyl-1-vinyl-3,8-dioxabicyclo[3.2.1]octane (333 mg, 1.6 mM) in methylene chloride (30 ml) and triethylamine (2 ml) at 0° C. and stirred for five minutes. The resulting mixture is treated with methanol (1 ml) and most of the solvent is removed in vacuo. The residue is filtered through a silica gel (20 g) column and washed with ether-petroleum ether (1:1, 300 ml). The solvent is removed in vacuo to give (1RS,4SR,5RS)-4-(3-methanesulfonyloxypropyl)-4-methyl-1-vinyl-3,8-dioxabicyclo[3.2.1]octane (408 mg, 90%) as a colorless oil.

Provenance & Evidence