Hexane → 5-Ethenyl-2-(trifluoromethyl)pyridine

Participants

Reaction Steps

A suspension of methyltriphenylphosphonium bromide (24.4 g, 68.4 mmol) in THF (150 mL) at −78° C. under an atmosphere of nitrogen was added 2.5 M of n-butyllithium in hexane (27 mL, 67.5 mmol) during a period of 12 mins. The reaction was warmed to room temperature to give a deep red ylide solution. To the ylide solution, cooled in ice, was introduced a solution of 6-(trifluoromethyl)nicotinaldehyde (10 g, 57 mmol) in THF (50 mL). The reaction mixture was warmed to room temperature and stirred for 3 hours. The result suspension was heated to 60° C. over 30 minutes and then stirred at 60° C. for 1 hour. After cooling, the mixture was diluted with water (400 mL), and extracted with EtOAc. The organic layer was washed with brine, dried (MgSO4), and concentrated. The residue was purified by silica gel column (0-10% EtOAc/hexane) to afford title compound.

Provenance & Evidence