Sodium hydride → 2-Benzoyl-4-oxo-4-pyridin-3-yl-butyronitrile

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Reaction Steps

To 3.0 g (21 mmol) of benzoyl acetonitrile in 50 mL of THF, cooled in a wet ice bath, was added 0.84 g (21 mmol) of sodium hydride (60% oil dispersion). After 1 h, added 2.8 g (10 mmol) of 3-bromoacetylpyridine hydrobromide. After 3 h, poured the reaction mixture into brine, extracted with ethyl acetate, dried over sodium sulfate, concentrated under reduced pressure and purified by flash chromatography (gradient elution: 40-80% ethyl acetate/hexane) to give 2.6 g (93%) of 2-benzoyl-4-oxo-4-pyridin-3-yl-butyronitrile (MH+=265).

Provenance & Evidence