Sodium → 2-(3-Trifluoromethylphenyl)-3-amino-5-phenyl-2-cyclopentenone

Participants

Reaction Steps

A dry 500-ml, three-neck, round-bottomed flask equipped with a mechanical stirrer, addition funnel and a reflux condenser bearing a nitrogen inlet tube was charged with 75 ml of methanol and 4.0 g of sodium. After all the sodium had reacted, a solution containing 38.4 g of [a-(3-trifluoromethyl-benzylcarbonyl)benzyl]acetonitrile in 75 ml of methanol was added rapidly dropwise while the reaction mixture was stirred at reflux. Reflux was continued for about 16 hours after which time the reaction mixture was concentrated in vacuo. The residue was dissolved in diethyl ether and washed once with 10% hydrochloric acid. The aqueous phase was back extracted (2X) with ether and the combined organic layers were dried over magnesium sulfate and concentrated to yield a red paste. The paste was triturated with ether to yield 7.8 g of the title compound as a pale yellow solid, (MP 205° to 206° C.).

Provenance & Evidence