CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][O:24][CH2:25][O:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][C:32]=1[CH:33]([OH:35])[CH3:34].C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[CH3:23][O:24][CH2:25][O:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][C:32]=1[C:33](=[O:35])[CH3:34]Dess-Martin periodinane (18 g, 43 mmol) was added to a stirring mixture of 1-(3-(methoxymethoxy)pyridin-4-yl)ethanol (4.6 g, 25 mmol), NaHCO3 (6.3 g, 75 mmol), and CHCl3 (75 mL) at RT. After 24 h, 1.0 M aqueous Na2S2O3 was added, the reaction mixture was stirred for 90 min, partitioned between ethyl acetate and 1.0 M aqueous Na2S2O3, the layers were separated, the organic layer was washed with 1.0 M aqueous Na2S2O3, water, brine, dried (Na2SO4), filtered, and the filtrate was concentrated. The residue was purified by flash chromatography on silica gel (gradient elution; 2:1→1:1 hexane-ethyl acetate) to give 3.9 g (86%) of 1-(3-(methoxymethoxy)pyridin-4-yl)ethanone as a clear yellow-orange oil.
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