Acetonitrile → N-(3-Phenylpropyl)acetamide

Participants

Reaction Steps

To a stirred suspension of morpholinodifluorosulfinium tetrafluoroborate (362 mg, 1.5 mmol) in acetonitrile (3.0 mL) at room temperature was added 3-phenylpropanol (131 μL, 1.0 mmol). After 1.5 h, the reaction mixture was quenched at room temperature with a 5% aqueous sodium bicarbonate solution, stirred for 15 minutes, and the resulting mixture was extracted twice using dichloromethane. The organic phases were combined, dried over magnesium sulfate and filtered through a pad of silica gel. Solvents were evaporated and the resulting crude material was purified by silica gel flash chromatography using DCM/MeOH (100/1) to provide 3-phenylpropanol (25 mg, 19%) and N-acetyl-3-phenylpropylamine (33 mg, 25%) as clear oils. Characterization for the latter: 1H NMR (CDCl3, 300 MHz) δ 7.31-7.08 (m, 5H), 5.60 (brs, 1H), 3.25 (q, J=6.8 Hz, 2H), 2.63 (t, J=7.7 Hz, 2H), 1.91 (s, 3H), 1.76 (m, 2H); 13C NMR (CDCl3, 75 MHz) δ 170.1, 141.4, 128.5, 128.3, 126.0, 38.3, 33.3, 31.1, 23.3.

Provenance & Evidence