[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]=[C:9]2[CH2:18][OH:19])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][N:10]=[C:9]2[CH:18]=[O:19])=[CH:6][CH:7]=1A solution of ethyl 1-(4-fluorophenyl)-2-(hydroxymethyl)-1H-imidazole-5-carboxylate (15) (210 mg, 0.80 mmol), and Dess-Martin Periodinane (DMP) (562 mg, 1.32 mmol) in dichloromethane (8 mL) was stirred at room temperature for 1 h. The reaction was added to a 1:1 mixture of Na2S2O3 (10% aq.) and NaHCO3 (sat.), then extracted with dichloromethane. The combined organic layers were washed with water, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (0-30% EtOAc in hexanes) to give ethyl 1-(4-fluorophenyl)-2-formyl-1H-imidazole-5-carboxylate (16).
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