Piperidine → Methyl 2-(4-fluorobenzylidene)-3-oxopentanoate

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Reaction Steps

A mixture of para-fluorobenzaldehyde (37.98 gm, 306 mmol), 3-oxopentanoic acid, methyl ester (39.78 gm, 306 mmol), piperidine (2.60 gm, 30.6 mmol) and HOAc (0.555 gm, 9.2 mmol) was allowed to reflux in benzene (150 ml) 7 hours under argon. The solution was cooled to room temperature, then diluted with ether and washed with 2% HCl, saturated NaHCO3, water, and brine, then dried over MgSO4, filtered and concentrated to give a yellow oil. The oil was purified by distillation (bp=144° C. at 2.7 mm Hg) to give the title compound as a yellow oil (50.612 gm, 70%).

Provenance & Evidence