[O:1]1[C:10]2[C:5](=[N:6][C:7](C#N)=[CH:8][CH:9]=2)[O:4][CH2:3][CH2:2]1.[CH3:13][Li].S(=O)(=O)(O)O.[C:20](=[O:23])([O-])O.[Na+]>O1CCCC1>[O:1]1[C:10]2[C:5](=[N:6][C:7]([C:20](=[O:23])[CH3:13])=[CH:8][CH:9]=2)[O:4][CH2:3][CH2:2]1
Under an argon atmosphere, 2,3-dihydro-[1,4]dioxino[2,3-b]pyridine-6-carbonitrile (16 mg, 99 μmol) was dissolved in tetrahydrofuran (500 μL), added methyllithium (150 μL (1.04 M in THF solution), 148 μmol) under ice-cold conditions, and the mixture was stirred at the same temperature for 5 minutes. The reaction solution was added 1M-sulfuric acid (2.0 mL), and stirred at room temperature for 3 hours. Under ice-cold conditions, the reaction solution was added a saturated aqueous solution of sodium hydrogen carbonate (pH=8 was confirmed). The reaction solution was extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and the title compound (8.3 mg (yield 47%)) was obtained as a yellow oil.
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