Hydrochloric Acid → 4-(1-Benzylthio-1-methylethyl)-2-methylene-4-butanolide

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Reaction Steps

To a solution of 2-benzylthio-2-methylpropionaldehyde (3.26 g) in THF (80 ml), zinc dust (2.56 g) activated with hydrochloric acid and a small amount of iodine were added. To the mixture methyl 2-bromoacrylate (3.00 g) dissolved in THF (20 ml) was added dropwise. The mixture was stirred for 3 hours under ultrasonic irradiation and filtrated by celite. To the filtrate ether was added. The organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The oily residue was purified by silica gel column chromatography to give 4.31 g (97%) of the titled compound.

Provenance & Evidence