Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH:9]([O:12][CH3:13])[O:10][CH3:11])=[C:4]([CH3:14])[N:3]=1.C([Li])CCC.CN(C)[CH:22]=[O:23].O>O1CCCC1>[CH3:11][O:10][CH:9]([O:12][CH3:13])[C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([CH:22]=[O:23])=[N:3][C:4]=1[CH3:14]To a solution of 2-bromo-5-dimethoxymethyl-3,6-dimethylpyridine (382 mg, 1.47 mmol) in tetrahydrofuran (6 mL) were added n-butyllithium (1.6 mol/L; 1,4 mL, 2.2 mmol) and dimethylformamide (0.23 mL, 3.0 mmol) sequentially at −78° C. under nitrogen atmosphere, and the mixture was stirred for 40 min. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was combined, washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (6:1 hexane/ethyl acetate) to afford 5-dimethoxymetyl-3,6-dimethyl-2-pyridinecarboxaldehyde (109 mg, 35%).
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