Isopropanol → 3-Chloro-2-isopropoxypyridine

Participants

Reaction Steps

iso-Propanol (128 mL; 1.07 mol) was added dropwise over 50 minutes to a suspension of sodium hydride (64.10 g; 1.07 mol) in THF (1.65 L) at 5° C. The reaction mixture was then warmed to room temperature and stirred for 1 hour. 2,3-Dichloropyridine (154.6 g; 1.11 mol) was added and the reaction mixture was heated to a gentle reflux and left to stir for 18 hours. The reaction mixture was cooled to 5-10° C. and carefully quenched with a brine: water mixture (50:50; 100 mL) followed by water (300 mL). The aqueous layer was extracted with EtOAc (3×600 mL). The combined organics were washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated to afford the title compound as a dark red oil (164.1 g, 89%):

Provenance & Evidence