Pyridine → 1-chloro-4-phenylbutan-4-one O-methyloxime

Participants

Reaction Steps

A mixture of 1-chloro-4-phenylbutan-4-one (1.83 g, 10 mmol), O-methylhydroxylammonium chloride (1.67 g, 20 mmol), pyridine (1.21 ml, 15 mmol), and ethanol (15 ml) was heated at reflux for 1 hour and then evaporated in vacuo. The residue was partitioned between chloroform and water, and the organic layer was dried (MgSO4) and evaporated in vacuo to give 1-chloro-4-phenylbutan-4-one O-methyloxime (1.78 g, 84%), νmax (neat) 2930, 1445, 1050, 900 cm-1 ; λmax (EtOH) 209 nm (εm 17,200), 253 nm (εm 11,100); δH (CDCl3) 7.3-7.8 (5H, m, aryl), 3.9 (3H, s, OMe), 3.5 (2H, t, H1), 2.9 (2H, t, H3), 2.0 (2H, qn, H2).

Provenance & Evidence