Sodium hydride → (2E)-1,2,6,7-tetrahydro-8H-cyclopenta[b]furo[3,2-d]pyridin-8-ylideneacetonitrile

Participants

Reaction Steps

To a solution of diethyl cyanomethylphosphonate (757 mg, 4.27 mmol) in tetrahydrofuran (20 mL) was added 65% sodium hydride (137 mg, 3.71 mmol) under ice-cooling, and the mixture was stirred at room temperature for 30 min. The mixture was added to a solution of 1,2,6,7-tetrahydro-8H-cyclopenta[b]furo[3,2-d]pyridin-8-one (500 mg, 2.85 mmol) in tetrahydrofuran (10 mL) under ice-cooling, and the mixture was stirred for 10 min. The reaction solution was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was 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 recrystallization (ethyl acetate) to give the title compound (337 mg, yield 60%).

Provenance & Evidence