Ethanethiol → (2R,4R)-2-(4-hydroxyphenyl)-4-decanolide

Participants

Reaction Steps

To a solution of 1.6 g of aluminium chloride and 2 ml of ethanethiol in 15 ml of dichloromethane was added, at 0° C, a solution of 440 mg of (2R,4R)-2-(4-methoxyphenyl)-4-decanolide dissolved in 5 ml of dichloromethane. This mixture was stirred for 4 hours. A saturated sodium bicarbonate aq. solution was then added, and the resulting mixture was subjected to extraction with dichloromethane, followed by column chromatography (Kieselgel 60, hexane/ethyl acetate = 3/1), thereby obtaining 374 mg (yield 90%) of (2R,4R)-2-(4-hydroxyphenyl)-4-decanolide. Identification data for this product are as follows. Melting point 87-88° C. [α]D20 +3.2° (c=1.27, MeOH).

Provenance & Evidence