The general procedure for the synthesis of 1,2-bis(4-pyridyl)ethene from 4-methylpyridine and 4-pyridinecarboxaldehyde was as follows: 400 μL (4.12 mmol) of 4-methylpyridine was reacted with 3.0 mL (4.32 mmol) of a solution of LDA in THF (5 mL) at -70 °C. Under light-avoiding conditions, 465 μL (4.12 mmol) of 4-pyridinecarboxaldehyde was added by continuous stirring and slow dropwise addition. Subsequently, the reaction mixture was refluxed in the presence of 10 mL of acetic acid for 24 h. The reaction mixture was observed to transform into a yellow solution. The light yellow solid product was isolated from this solution by rotary evaporation. Purification of the solid product using column chromatography under similar conditions afforded 368 mg (49% yield) of the target compound.1H NMR (400 MHz, CDCl3, δ): 8.62 (d, J = 4Hz, 4H, Ar-H), 7.61 (d, J = 4Hz, 4H, Ar-H), 7.55 (s, 2H, -CH=CH-).
