Acetic Acid → 4-(2,2-Dimethylpropionyl)-3-hydroxy-5-(2-methoxycarbonylmethyloxyphenyl)-1-(4-thiophene-3-ylphenyl)-1,5-dihydropyrrole-2-one

Participants

Reaction Steps

A mixture of ethyl trimethylacetopyruvate (0.40 g, 2 mmol), 4-thiophene-3-ylaniline (0.35 g, 2 mmol), 2-(methoxycarbonylmethyloxy)benzaldehyde (0.39, 2 mmol), acetic acid (0.057 mL, 1 mmol) and dioxane (4 mL) was heated at reflux overnight. After the reaction was completed, saturated sodium bicarbonate solution and brine were poured into the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulphate, and then concentrated in vacuo. The resulting residue was purified on a silica gel column chromatography (methanol/chloroform), and the aimed compound was triturated with ethyl acetate and diisopropyl ether to give 4-(2,2-dimethylpropionyl)-3-hydroxy-5-(2-methoxycarbonylmethyloxyphenyl)-1-(4-thiophene-3-ylphenyl)-1,5-dihydropyrrole-2-one (0.42 g, yield: 41%) as pale brown solid.

Provenance & Evidence