Hexane → 2-Methyl-5-vinylpyridine

Participants

Reaction Steps

To a suspension of methyltriphenylphosphonium bromide (62.54 g, 0.175 mol) in THF (150 mL) at −78° C. under nitrogen was added 2.5 M of n-butyllithium in hexane (69 mL, 0.17 mol) over a period of 1 hr. The mixture was warmed to room temperature to give a deep yellow ylide solution. To the ylide solution, cooled in ice, was introduced a solution of 6-methylnicotinaldehyde (18.63 g, 0.146 mol) in THF (50 mL). The reaction mixture was warmed to room temperature and stirred for 2 hours. The resulting suspension was heated to 60° C. over 30 minutes and stirred at 60° C. for 1 hour. After cooling, the reaction mixture was diluted with water and extracted with EtOAc. The organic layer was separated and washed with brine, dried (MgSO4), and concentrated. The residue was purified by silica gel column (0-10% EtOAc/hexane) to afford the title compound.

Provenance & Evidence