Thiophenol → Methyl 2-methylthio-3-(phenylthio)acrylate

Participants

Reaction Conditions

Reaction Steps

3.50 g (11.6 mmol) of methyl 2-(methylthio)-3-(p-toluenesulfonyloxy)-2-propenoate was dissolved in 20 ml of chloroform and cooled to 0° C. To the solution was added 1.28 g (11.6 mmol) of thiophenol and 2 ml (14.3 mmol) of triethylamine and stirred at room temperature for 1 hour. To the reaction mixture was added tert-butyl methyl ether and washed sequentially with an aqueous 1N NaOH solution and a saturated NaCl solution. The organic layer was dried and then concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1) to obtain 1.64 g of methyl 2-(methylthio)-3-(phenylthio)-2-propenoate.

Provenance & Evidence