Hydrochloric Acid → 1,2,6,7-tetrahydro-8H-cyclopenta[b]furo[3,2-d]pyridin-8-one

Participants

Reaction Conditions

Reaction Steps

To a suspension of 65% sodium hydride (1.38 g, 37.4 mmol) in tetrahydrofuran (10 mL) were added a solution of methyl 5-(3-methoxy-3-oxopropyl)-2,3-dihydrofuro[2,3-c]pyridine-4-carboxylate (1.98 g, 7.46 mmol) in tetrahydrofuran (80 mL) and methanol (0.2 mL), and the mixture was stirred at 80° C. for 10 min. 12M Hydrochloric acid (40 mL) was added thereto under ice-cooling, and the organic solvent was evaporated under reduced pressure. The residual aqueous solution was stirred at 150° C. for 20 min, the reaction mixture was basified with 8M aqueous sodium hydroxide solution under ice-cooling, and extracted with ethyl acetate. The extract was 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=10/90→40/60) to give the title compound (886 mg, yield 68%).

Provenance & Evidence