Methyl iodide → 4-(1-Methoxyethyl)pyridine

Participants

Reaction Steps

A solution of 8.4 g (0.068 mol) of 4-(1-hydroxyethyl)pyridine in 20 ml of absolute tetrahydrofuran is added dropwise to a suspension of 2 g (0.083 mol) of sodium hydride (3.3 g of 60% oil dispersion; washed in toluene) in 80 ml of absolute tetrahydrofuran. After the development of hydrogen has ceased, 23 g (0.16 mol) of methyliodide are added at 18°-20° C. and the mixture is left to react for 2 hours. The reaction mixture is concentrated by evaporation, the residue is combined with 40% aqueous potassium carbonate solution and extracted with ether. The organic phase is separated, dried over sodium sulphate and concentrated by evaporation. After distillation of the crude product at 82°-85° C./20 mbar, 5.2 g (55.6% of theory) of the title compound are obtained.

Provenance & Evidence