Water → 3-[(Cyclopent-3-en-1-yl)methyl]pyridin-2(1H)-one

Participants

Reaction Steps

To a cloudy dispersion containing 3-(cyclopent-3-en-ylmethyl)-2-(methyloxy)pyridine (Preparation 28, 2.1 g, 11.1 mmol) and sodium iodide (4.1 g, 27.8 mmol) in anhydrous acetonitrile (25 ml) was added chlorotrimethylsilane (3.0 g, 27.8 mmol). A white precipitate formed which was stirred for 30 min at room temperature and then for 1 h at 70° C. The reaction mixture was cooled to room temperature and water was added, followed by ethyl acetate (200 ml), the organic layer washed with water (4×) and then with sodium hydrogen carbonate solution and brine before drying (Na2SO4) to give the title compound as a yellow solid (1.93 g, 100%).

Provenance & Evidence