Diethyl Malonate → Diethyl 2-(3'-{[methyl-(1-phenylmethanoyl)amino]methyl}biphenyl-4-ylmethylene)malonate

Participants

Reaction Steps

600 mg (1.8 mmol) of N-(4′-formylbiphenyl-3-ylmethyl)-N-methylbenzamide (prepared as in Example 1(e)), 10 ml of toluene, 300 μl (1.8 mmol) of diethyl malonate and 50 mg (0.35 mmol) of piperidine acetate are introduced into a three-necked flask under a stream of nitrogen. This mixture is refluxed for 6 hours, while separating out the water formed using Dean-Stark apparatus. The reaction medium is cooled, extracted with ethyl acetate and washed with water. The organic phase is separated out after settling has taken place, dried over magnesium sulfate and evaporated. The crude product is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (75/25). After evaporation of the solvents, 700 mg (84%) of expected product are collected.

Provenance & Evidence