Diethyl Ether → 103028-75-7

Participants

Reaction Steps

A solution of 2-cyano-4-methylpyridine (526 mg, 4.45 mmol) in Et2O (10 mL) added over 10 min to a rapidly stirring solution of freshly prepared n-PrMgBr (from n-PrBr (0.40 mL, 4.45 mmol) and Mg (132 mg) in Et2O (10 mL). Once addition was completed, the reaction was heated to reflux in a warm water bath for 2 hours. The reaction was cooled to RT then cooled in ice, quenched with 1 mL H2O then 13 mL 5N H2SO4. The ether phase was separated. The aqueous phase was heated in warm water for 15 minutes, then cooled in ice and basified with sat. K2CO3. The solution was extracted with CHCl3 and dried over K2CO3. The solution was filtered and concentrated to afford 372 mg of 1-(4-methylpyridin-2-yl)butan-1-one as an oil: 1H NMR (400 MHz, CDCl3) δ ppm 8.51 (d, J=4.80 Hz, 1H), 7.85 (s, 1H), 7.27 (s, 1H), 3.17 (t, J=7.45 Hz, 2H), 2.41 (s, 3H), 1.69-1.79 (m, J=7.43, 7.43, 7.43, 7.43, 7.43 Hz, 2H), 0.99 (t, J=7.45 Hz, 4H).

Provenance & Evidence