Isopropanol → 3-Chloro-2-isopropoxypyridine

Participants

Reaction Conditions

Reaction Steps

To a 3-necked flask equipped with a dropping funnel, thermometer and a condenser was added sodium hydride (64.10 g; 1.07 mol) followed by THF (1.65 L). The suspension was cooled to 5° C. and iso-propanol (128 mL; 1.07 mol) was added dropwise over 50 minutes. Upon complete addition the ice bath was removed and the mixture was brought to room temperature and was left to stir for 1 hour. Then 2,3-dichloropyridine (154.6 g; 1.11 mol) was added and the reaction mixture brought to a gentle reflux and left to stir for 18 hours. The reaction mixture was cooled to 5-10° C. and was carefully quenched with brine:water mixture (50:50; 100 mL) followed by water (300 mL). The aqueous layer was extracted with EtOAc (3×600 mL), the organic layers combined and washed with brine, dried (MgSO4), filtered and evaporated to give the title compound as a dark red oil (164.1 g; 89%).

Provenance & Evidence