Ethanol → Ethyl 5-phenylnicotinate

Participants

Reaction Steps

A mixture of methyl 5-trifluoromethanesulfonyloxy-3-pyridinecarboxylate (18.00 g), phenylboronic acid (7.88 g), tetrakis(triphenylphosphine)palladium (3.01 g), sodium carbonate (13.51 g), ethanol (80 ml), water (80 ml) and toluene (500 ml) was refluxed overnight under an argon atmosphere. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain ethyl 5-phenyl-3-pyridinecarboxylate (8.63 g, yield 60%) as a colorless oily substance from the fraction eluted with ethyl acetate.

Provenance & Evidence