Methyl propiolate → HCID 86644386, compound

Participants

Reaction Steps

To a solution of methyl propiolate (0.75 mL) in THF (10 mL) were added a solution of benzene-1,2-dithiol (1.2 g) in THF (10 mL) and tert-butoxy potassium (catalytic amount) under ice-cooling, and the mixture was stirred at the same temperature for 3 hours and then at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure. To the residue was added methanol (5 mL) at room temperature, and then an aqueous solution (10 mL) of sodium hydroxide (0.45 g). The mixture was stirred at 80° C. for 2 hours. To the reaction mixture was added ion-exchanged water (20 mL), which was washed with ethyl acetate. The aqueous layer was adjusted to pH 2 by addition of 1N hydrochloric acid, and then extracted with ethyl acetate (70 mL) twice. The organic layers were combined, washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 2-(benzo[1,3]dithiol-2-yl)acetic acid (1.35 g) as a yellow crystal.

Provenance & Evidence