Ethyl Acetoacetate → HCID 67313979, compound

Participants

Reaction Conditions

Reaction Steps

An ice cooled solution of ethyl acetoacetate (0.21 ml, 1.63 mmol) in 10 ml ethanol was treated with a solution of sodium ethanolate 21% (in ethanol, 0.6 ml, 1.63 mmol). The reaction mixture was stirred 1 h at 0° C., then N-[3-(trifluoromethyl)phenyl]pyridine-4-carbohydrazonoyl bromide (562 mg, 1.63 mmol) in 5 ml ethanol was added drop wise. The yellow suspension was stirred 1 h at room temperature and 2 days at 50° C. The reaction mixture was concentrated in vacuo and the residual product partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The organic phases were dried over magnesium sulfate and evaporated. Column chromatography (EtOAc:n-heptane 1:1) gave the title compound as a light brown oil (130 mg, 21%). MS: 376.5 (MH+).

Provenance & Evidence