[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:4][CH:3]=1.Cl.Cl[C:18]1[CH:19]=[C:20]([CH2:24][NH:25][OH:26])[CH:21]=[CH:22][CH:23]=1.C([O-])(=O)C.[Na+].C(O)(=O)C.C(=O)(O)[O-].[Na+]>C(O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N+:25]([O-:26])[CH2:24][C:20]2[CH:21]=[CH:22][CH:23]=[CH:18][CH:19]=2)[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:4][CH:3]=1A 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.
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