Phosphorus oxychloride → 4-Chlorofuro[3,2-c]pyridine

Participants

Reaction Conditions

Reaction Steps

Furo[3,2-c]pyridin-4(5H)-one (72.2 g, 534 mmol) was added to phosphorus oxychloride (100 mL) heated to 120° C., and the mixture was stirred for 30 min. The solvent was evaporated under reduced pressure. Ice-cooled water was added to the residue, and the mixture was basified with 8M aqueous sodium hydroxide solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70) to give the title compound (66.1 g, yield 81%).

Provenance & Evidence