Methyl Benzoate → 1-(1-Methylpyrrol-2-yl)-3-phenyl-1,3-propanedione

Participants

Reaction Conditions

Reaction Steps

To a stirred, cooled (5° C.) slurry of 0.96 g (0.04 mol) of hexane-washed sodium hydride in 2.72 g (0.02 mol) of methyl benzoate under nitrogen was added a solution of 5.0 g (0.04 mol) of 2-acetyl-1-methylpyrrole in 30 mL of ethyl ether. A few drops of ethanol were added. The reaction mixture was allowed to stir at 5° C. for 12 h. The mixture was poured into water and extracted with ethyl ether. The combined organic layers were washed with brine, dried over magnesium sulfate, and filtered. Removal of solvents gave a waxy solid which was purified by flash-chromatography (silica gel, ethyl acetate/hexane as eluent) to give 0.8 g of 1-(1-methylpyrrol-2-yl)-3-phenyl-1,3-propanedione.

Provenance & Evidence