Water → HCID 22841017, compound

Participants

Reaction Steps

1.04 ml of an approximately 28% w/v methanolic solution of sodium methoxide was added dropwise at -10° C. to 1.422 g of dl-S-(cis-2-benzyloxymethyltetrahydropyran-3-yl) thioacetate (prepared as described in Preparation 38) dissolved in 30 ml of methanol. The reaction mixture was stirred at -10° to 0° C. for 2 hours, and then 0.33 ml of methanesulfonic acid was added. The reaction mixture was then poured into water and extracted with ethyl acetate. The extracts were washed with water, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure to give an oily residue. The residue was subjected to column chromatography through 30 g of silica gel. Those fractions eluted with mixtures of diethyl ether and hexane ranging from 3:97 to 5:95 by volume were worked up, to give 1.146 g of the title compound as an oil.

Provenance & Evidence