Neopentyl alcohol → 2,2-Dimethylpropyl 6-chloropyridine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 10 g (56.8 mmol) of 6-chloropyridine-3-carbonyl chloride in 100 mL of anhydrous toluene are added under argon, at room temperature, 15 g (170.4 mmol) of 2,2-dimethylpropanol. The reaction medium is then heated at 80° C. for 6 hours. After cooling to room temperature, the medium is concentrated and the residue obtained is taken up in 800 mL of EtOAc, washed successively with water (2×200 mL), with saturated NaHCO3 solution (2×200 mL) and with brine (100 mL), dried over Na2SO4, then concentrated under reduced pressure and purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc gradient of from 0 to 5% EtOAc. 11.9 g of 2,2-dimethylpropyl 6-chloropyridine-3-carboxylate are obtained in the form of a white powder.

Provenance & Evidence