Iodoethane → tert-Butyl 4-(3-(5-ethoxypyridin-2-yloxy)benzylidene)piperidine-1-carboxylate

Participants

Reaction Steps

To a stirred solution of tert-butyl 4-(3-(5-hydroxypyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (0.6 g, 1.56 mmol) in acetone (5 mL) was added ethyl iodide (0.304 g, 1.96 mmol), K2CO3 (0.431 g, 3.12 mmol) and 18-crown-6 (0.824 g, 3.12 mmol) at 0° C. The reaction mixture was stirred at RT overnight. The reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate three times. The organic layer was washed with fresh water and brine solution, dried over Na2SO4 and concentrated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (1:19 acetone:hexanes) to give the title compound (610 mg, 95%). 1H NMR (500 MHz, CDCl3): δ 7.86 (d, J=2.5 Hz, 1H), 7.27 (m, 2H), 6.96 (d, J=7.5 Hz, 1H), 6.90 (m, 2H), 6.85 (d, J=9 Hz, 1H), 6.32 (s, 1H), 4.02 (q, 2H, J=6.8), 3.49 (s, 2H), 3.38 (s, 2H), 2.45 (s, 2H), 2.30 (s, 2H), 1.47 (s 9H) 1.40 (t, J=6.92 Hz, 3H); m/z (411.51, M+ H+).

Provenance & Evidence