Acetic Acid → HCID 86742210, compound

Participants

Reaction Steps

A suspension of 2.00 g (0.0098 mol) of 1-(4-fluorophenyl)-2-(1H-imidazol-1-yl)ethanone (1, R1 =4-F), 1.30 g (0.011 mol) of N-(phenylmethyl)hydroxylamine (2, R2 =H), 0.82 g (0.010 mol) of sodium acetate, and 0.60 ml (0.010 mol) of acetic acid in 25 ml of ethanol is heated to reflux under a nitrogen atmosphere and stirred for 24 hours. Upon cooling to ambient temperature, the suspension is poured into 50 ml of water, neutralized with sodium bicarbonate and extracted with chloroform (2×50 ml). The combined organic extract is dried over anhydrous magnesium sulfate, concentrated in vacuo, and flash-chromatographed on neutral silica gel using a 9:1 by volume mixture of ethyl acetate and methanol as the eluent, to give 1.63 g (54%) of 1-(4-fluorophenyl)-2-(1H-imidazol-1-yl)-N-(phenylmethyl)ethanimine N-oxide (3, R1 =4-F, R2 =H) as a light yellow oil. This oil (0.0053 mol) is dissolved in 50 ml of toluene, 1.5 ml (0.013 mol) of styrene (4, R3 =C6H5) is added, and the solution is refluxed under a nitrogen atmosphere for 28 hours, cooled to ambient temperature and concentrated in vacuo. The resulting cis- and trans-diastereomeric mixture of compound 5 (R1 =4-F, R2 =H, R3 =C6H5) is flash-chromatographed on neutral silica gel using a 98.2 by volume mixture of chloroform and methanol as the eluent.

Provenance & Evidence