Hydrochloric Acid → 1-Carbamoyl-3-(3-ethoxy-4-hydroxybenzylidene)pyrrolidin-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 939 mg (2 mmol) of (1-carbamoyl-2-oxopyrrolidin-3-yl)triphenylphosphonium bromide in ethanol (16 ml) were added 332 mg (2 mmol) of 3-ethoxy-4-hydroxybenzaldehyde and 558 μl (4 mmol) of triethylamine, and the mixture was stirred at 60° C. for 2 hours. The reaction mixture was evaporated to give a residue, which was dissolved in diisopropyl ether and treated with 4 ml of 1N aq. sodium hydroxide. The aqueous layer was made acid with 1N hydrochloric acid under ice-cooling and the product was dissolved in ethyl acetate, washed with water and saturated brine, dried over magnesium sulfate and evaporated to give a residue, which was crystallized from a dichloromethane/n-hexane mixture to give 143 mg of the objective compound (Ia-19) in 26% yield.

Provenance & Evidence