Acetic Acid → 4-(2,2-dimethyl-3-tetrahydro-2H-pyrane-2-yloxypropionyl)-3-hydroxy-5-(2-methoxy-3-pyridyl)-1-(4-thiophene-3-ylphenyl)-1,5-dihydropyrrole-2-one

Participants

Reaction Steps

A mixture of methyl 5,5-dimethyl-2,4-dioxo-6-(tetrahydro-2H-pyrane-2-yloxy)hexanoate (0.29 mg, 1.0 mmol), 4-(3-thienyl)aniline (0.18 g, 1.0 mmol), 2-methoxynicotinaldehyde (0.14 g, 1.0 mmol), acetic acid (0.043 mL, 0.75 mmol) and dioxane (2 ml) was heated at reflux overnight. After the reaction was completed, the reaction mixture was concentrated in vacuo. The resulting residue was purified on a silica gel column chromatography (methanol/chloroform) to give 4-(2,2-dimethyl-3-tetrahydro-2H-pyrane-2-yloxypropionyl)-3-hydroxy-5-(2-methoxy-3-pyridyl)-1-(4-thiophene-3-ylphenyl)-1,5-dihydropyrrole-2-one (0.30 g, yield: 55%) as pale yellow solid.

Provenance & Evidence