Acetic Acid → 1-(4-bromophenyl)-4-(2,2-dimethyl-3-tetrahydro-2H-pyrane-2-yloxypropionyl)-3-hydroxy-5-(2-methoxyphenyl)-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 (4.29 g, 15 mmol), 4-bromoaniline (2.58 g, 15 mmol), 2-methoxybenzaldehyde (1.812 mL, 15 mmol), acetic acid (0.343 mL, 6 mmol) and dioxane (15 ml) was heated at reflux overnight. After the reaction was completed, the mixture was concentrated in vacuo and the resulting residue was purified on a silica gel column chromatography (ethyl acetate/n-hexane). The resulting aimed compound was triturated with ethyl acetate and n-hexane to give 1-(4-bromophenyl)-4-(2,2-dimethyl-3-tetrahydro-2H-pyrane-2-yloxypropionyl)-3-hydroxy-5-(2-methoxyphenyl)-1,5-dihydropyrrole-2-one (2.69 g, yield: 33%) as colorless solid.

Provenance & Evidence