Sodium Hydroxide → 4-Ethenylquinoline

Participants

Reaction Conditions

Reaction Steps

A solution of 4-quinolinecarboxaldehyde (5 g; 3.18×10-2 mol) in 32 ml of benzene, containing triphenylmethylphosphonium iodide (26 g; 6.36×10-2 mol), is added under an inert atmosphere to sodium hydroxide solution (96 ml; 5N). The two-phase system is stirred at 45° C. for 30 minutes. After allowing the phases to separate by settling, the aqueous phase is extracted with ethyl acetate (3×100 ml). The organic phases are combined and washed with 1N HCl solution (2×30 ml), then the aqueous phase is neutralized with NaHCO3 and extracted with methylene chloride (3×100 ml). The organic phase is dried over MgSO4. The desired product is purified by chromatography on a MERCK F254 silica column (eluent=cyclohexane/AcOEt, 8:2). Yield=2.8 g (60%).

Provenance & Evidence