FC(F)(F)C(OC(=O)C(F)(F)F)=[O:4].[Cl:14][C:15]1[C:16]([CH3:27])=[N+:17]([O-])[CH:18]=[C:19]([CH:21]2[O:25][CH2:24][CH2:23][O:22]2)[CH:20]=1.CO.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Cl:14][C:15]1[C:16]([CH2:27][OH:4])=[N:17][CH:18]=[C:19]([CH:21]2[O:25][CH2:24][CH2:23][O:22]2)[CH:20]=1Trifluoroacetic anhydride (231 μl, 1.635 mmol) was added to a solution of 3-chloro-5-(1,3-dioxolan-2-yl)-2-methylpyridine 1-oxide (225 mg, 1.043 mmol) in DCM (4 ml) at 0° C. and the mixture was stirred at room temperature for 48 h. Full conversion was observed by HPLC. MeOH (0.5 ml, 12.36 mmol) was added and, after stirring for 10 min, DCM and 10% Na2CO3 solution were added. Extraction, drying (MgSO4), and filtration afforded 223.2 mg of crude material. Purification by flash chromatography using Flashmaster II, a 5 g silica gel cartridge, and mixtures of hexane and EtOAc as eluent afforded [3-chloro-5-(1,3-dioxolan-2-yl)-2-pyridinyl]methanol (142.7 mg, 63%) as a yellow oil.
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