Methyl acetoacetate → HCID 14163608, compound

Participants

Reaction Conditions

Reaction Steps

Methyl acetoacetate (9.56 g, 82.3 mmole) is added dropwise to a stirred suspension of sodium hydride (50% oil suspension) (3.95 g, 82.3 mmole) in anhydrous tetrahydrofuran at 0° C. under a nitrogen atmosphere. The resulting solution is stirred 15 minutes at 0° C. and then treated with a 1.6 M solution (51.5 ml, 82.3 mmole) of n-butyllithium in hexane over 5 minutes. The resulting solution is stirred 15 minutes at 0° C. and then treated with a solution of (E)-2,4-dichloro-6-(4-fluorophenyl)cinnamaldehyde (82.3 mmole) in anhydrous tetrahydrofuran (150 ml). The resulting orange solution is stirred 15 minutes at 0° C. and then quenched by dropwise addition of 12 N hydrochloric acid (ca. 20 ml). The reaction mixture is diluted with water (100 ml) and extracted with ether (3×300 ml). The organic extracts are combined, washed with brine (3×100 ml), dried over magnesium sulfate and filtered. The filtrate is evaporated in vacuo leaving the title compound as an oil.

Provenance & Evidence