4-Vinylpyridine → 4-(2-Phenylvinyl)pyridine, trans-

Participants

Reaction Steps

A mixture of phenyl iodide (100 ml, 0.89mol), 4-vinylpyridine (115 ml, 1.07 mol), palladium acetate (2.4 g, 0.01 mol), tri-o-tolylphosphine (6.08 g, 0.02 mol) and triethylamine (150 ml, 1.07 mol) was refluxed for 3 hours. The reaction was cooled to room temperature, the resulting solid dissolved in dichloromethane (2 l) and washed with saturated aqueous sodium carbonate solution (2 l). The aqueous phase was further extracted with dichloromethane (3×1.5 l) and the combined organic phases dried (MgSO4) and evaporated. The resulting solid was washed with ethyl acetate (1.5 l), filtered and dried in vacuo to give (E)-4-(2-phenylethenyl)pyridine (90 g, 56%); δH (CDCl3) 7.01 (1H, d, J 16.3 Hz, ArCH=CH), 7.25-7.41 (6H, m, PhH, ArCH=CH), 7.53 (2H, d, J 5.3 Hz, 3-H, 5-H), and 8.58 (2H, d, J 5.2 Hz, 2-H, 6-H).

Provenance & Evidence