Phenyl-3-pyridinylmethanone → 3-Phenyl-3-pyridin-3-yl-acrylonitrile

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Reaction Steps

1 g (5.46 mmol, 1 eq) of 3-benzoylpyridine is dissolved in 30 ml of ethanol under Ar. 1.16 mL (7.10 mmol, 1.3 eq) of diethylcyanomethylphosphonate and 965 mg (14.1 mmol, 2.6 eq) of NaOEt are added. The mixture is stirred for 1 hour at room temperature. 108 mg (2.73 mmol, 0.5 eq) of 60% NaH in oil are added and the mixture is heated to 70-80° C. for 1 hour. A further 138 mg (3.49 mmol, 0.64 eq) of NaH are added and the mixture is heated for 40 min at 70-80° C. An NH4Cl solution is added, then the EtOH is concentrated. The basic aqueous phase is extracted with AcOEt and the organic phase is washed with brine, dried, filtered and concentrated. The oil obtained is subjected to chromatography over alumina (eluant: heptane/AcOEt: 7/1). A mixture of two stereoisomers is obtained (oil, m=1.076 g, yield=96%).

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