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To a suspension of sodium hydride (62% oil, 10.87 g) in tetrahydrofuran (200 ml) was added successively diethyl cyanomethylphosphonate (43.25 ml) and pyridine-3-carbaldehyde (24 ml) at 0° C. Then, the reaction mixture was heated to refluxing temperature. After 5 hours the reaction mixture was poured into a mixture of ethyl acetate (1 l) and water (200 ml). The organic layer was separated, washed with brine and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (600 ml) eluting with ethyl acetate to give 3-(3-pyridyl)acrylonitrile (23.9 g).

1. temperatureThen, the reaction mixture was heated
2. temperatureto refluxing temperature
3. customThe organic layer was separated
4. washwashed with brine
5. dry with materialdried over magnesium sulfate
6. customEvaporation of the solvent
7. customgave a residue, which
8. customwas chromatographed on silica gel (600 ml)
9. washeluting with ethyl acetate