[CH2:1]([C:8]1[S:12][C:11]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])=[N:10][C:9]=1[CH2:21][OH:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>ClCCl>[CH2:1]([C:8]1[S:12][C:11]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])=[N:10][C:9]=1[CH:21]=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1To a solution of (5-benzyl-2-(2,5-difluorophenyl)thiazol-4-yl)methanol (6.66 g, 20.99 mmol) in dichloromethane (70.0 mL) was added Dess-Martin periodinane (13.35 g, 31.5 mmol). The reaction mixture was stirred at room temperature for overnight. 200 mL of saturated NaHCO3 solution and saturated Na2S2O3 solution (8:1) was added for quenching the reaction. After stirred for 1 h, the reaction mixture was extracted by EtOAc. The organic layers was washed with water and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by column chromatography to yield 5-benzyl-2-(2,5-difluorophenyl)thiazole-4-carbaldehyde (5.3 g, 80%) as white solid. 1H NMR (CDCl3, 400 MHz): δ 10.3 (1H, s), 8.01 (1H, m), 7.36-7.17 (5H, m), 7.16-7.07 (2H, m), 4.64 (2H, s). LC/MS (uplc): MH+ 316.2, 1.21 min.
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