Water → HCID 13832674, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of [(3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methanol (J. Heterocycl. Chem., 13 1966, 485) (43.1 g, 0.21 mol) in dry tetrahydrofuran (400 ml), at 0° C. and under an atmosphere of nitrogen, was carefully treated with sodium hydride, (7.7 g of an 80% dispersion in mineral oil, 0.26 mol). The resultant mixture was warmed to room temperature and stirred for 1 hr. The reaction mixture was cooled to 0° C. and a solution of methyl iodide (15.8 m, 0.25 mol) in dry tetrahydrofuran (30 ml) added slowly. The resultant mixture was stirred for a further 30 min at 0° C. and then at room temperature for 24 hr. Water (1000 ml) was added carefully and the mixture extracted with diethyl ether (3×500 ml). The combined organic extracts were washed with brine, dried with anhydrous magnesium sulfate, filtered and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a solvent system of diethyl ether:pentane (1:4), to afford the title compound as an oil (36.5 g).

Provenance & Evidence