Water → 3-Benzyloxy-2-methoxypropylthioalcohol

Participants

Reaction Steps

To a solution of 14.028 g (55 mM) of acetylthio-3-benzyloxy-2-methoxypropane VII 6 in 300 ml of methanol is added dropwise 11.24 ml (58.3 mM) of 28 weight % solution of sodium methoxide in methanol at -10° C. After the mixture is stirred at -10° C. to 0° C. for 2 hours, 3.58 ml of methanesulfonic acid is added. The reaction mixture is poured into water and the product is isolated by ethyl acetate extraction. The ethyl acetate layer is washed with water, dried, and evaporated. The oily residue is purified by column chromatography on silica gel using an ether-n-hexane (3:97) mixture as an eluent to give 8.85 g (41.7 mM) of the titled compound, 3-benzyloxy-2-methoxypropylthioalcohol VII 6 as an oil.

Provenance & Evidence