Methanol → 5,6-Dihydro-7H-cyclopenta[c]pyridin-7-one

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Reaction Steps

A solution of methyl 4-(3-ethoxy-3-oxopropyl)nicotinate (4.80 g, 20.2 mmol) in tetrahydrofuran (100 mL) was added to a suspension of 60% sodium hydride (3.73 g, 93.3 mmol) in tetrahydrofuran (50 mL) at room temperature. Methanol (100 μL) was added to the mixture at room temperature, and the mixture was heated under reflux for 4 hr. After cooling to room temperature, the mixture was concentrated under reduced pressure. The residue was added to 12M hydrochloric acid (50 mL) at 0° C., and the mixture was stirred at 110° C. for 30 min. The mixture was alkalified with sodium hydrogen carbonate, the insoluble material was filtered off, and the filtrate was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with hexane to give the title compound (1.57 g, yield 58%).

Provenance & Evidence