Water → 1-(4-Pyridinyl)-1-propanone

Participants

Reaction Steps

To a solution of 2.845M ethylmagnesium bromide (263 mL, 0.75 mol) in ethyl ether (Et2O) (250 mL) was slowly added a solution of 4-cyanopyridine (39 g, 0.375 mol) in Et2O (750 mL). The reaction mixture was warmed at reflux for 12 hours, treated with concentrated H2SO4 (125 mL)/H2O (125 mL), and then washed three times with Et2O (250 mL). The aqueous portion was made basic (pH 9) with 15% NaOH solution and extracted five times with 250 mL portions of Et2O. The combined Et2O extracts were dried (MgSO4), and the solvent was removed under reduced pressure to afford a brown oil (48.4 g, 95%). Purification by vacuum distillation at 93°-97° (2.6 mm) afforded product as a pale yellow oil (25.35 g, 50%), NMR (CDCl3) δ 1.23 (t, 3H, J= 7 Hz), 3.00 (q, 2H, J=7 Hz), 7.70 (d, 2H, J=6 Hz), and 8.78 (d, 2H, J=6 Hz); IR (film) 1695 cm-1.

Provenance & Evidence