Diethyl Ether → 2,6-Diethyl-pyridine

Participants

Reaction Steps

A solution of ethylmagnesium bromide in ethyl ether [prepared from Mg (16.5 g, 0.68 mol) and ethyl bromide (50 mL, 0.68 mol) in 500 mL of ether] was added dropwise to a mixture of 2,6-dichloropyridine (50 g, 0.34 mol) and NiCl2(dppp) (1.0 g, 2 mol) in anhydrous ethyl ether (500 mL) at 0° C. under N2 atmosphere. After addition, the resulting mixture was stirred at ambient temperature overnight, was then heated to reflux for about 3 hours. The suspension was poured into crushed ice (200 g) and the mixture was saturated with NH4Cl. The organic layer was separated and the aqueous phase was extracted with ether (200 mL×3). The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated to give the product (41.1 g, 89%).

Provenance & Evidence