Diethyl Ether → 2-Benzyl-6-methoxypyridine

Participants

Reaction Steps

A Grignard's reagent prepared from 123 ml of benzyl bromide, 30 g of magnesium and 400 ml of diethylether was slowly added dropwise into a mixture of 150 g of 2-bromo-6-methoxypyridine, 4.3 g of 1,3-bis(diphenylphosphino)propanenickel(II) chloride and 500 ml of tetrahydrofuran under stirring in an ice bath. After stirring overnight as it was, the mixture was extracted with an aqueous ammonium chloride solution and hexane. The organic phase was washed with water and then brine, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using 1% and 1.5% of ethyl acetate/hexane, to give 150 g of the target compound.

Provenance & Evidence