[CH2:1]([C:3]1[CH:4]=[C:5]([C:11](=O)[CH3:12])[CH:6]=[CH:7][C:8]=1[CH2:9][OH:10])[CH3:2].[CH:14]1([C:20]2[CH:28]=[CH:27][C:23]([CH2:24][O:25][NH2:26])=[CH:22][C:21]=2[C:29]([F:32])([F:31])[F:30])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(O)(=O)C>CO>[CH:14]1([C:20]2[CH:28]=[CH:27][C:23]([CH2:24][O:25][N:26]=[C:11]([C:5]3[CH:6]=[CH:7][C:8]([CH2:9][OH:10])=[C:3]([CH2:1][CH3:2])[CH:4]=3)[CH3:12])=[CH:22][C:21]=2[C:29]([F:30])([F:31])[F:32])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1To a solution of 1-(3-ethyl-4-hydroxymethyl-phenyl)-ethanone (1 eq) in methanol is added O-(4-cyclohexyl-3-trifluoromethyl-benzyl)-hydroxylamine (1 eq) followed by the addition of acetic acid (0.05 eq). The mixture is stirred at room temperature for 12 hours. After concentration, the residue is purified by column chromatography (30% EtOAc in hexane) to give 1-(3-ethyl-4-hydroxymethyl-phenyl)-ethanone O-(4-cyclohexyl-3-trifluoromethyl-benzyl)-oxime as an oil [MS: (ES+) 434.2 (M+1)+].
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