[O:1]1[C:5]2=[CH:6][N:7]=[C:8]([CH:10]=[O:11])[CH:9]=[C:4]2[CH:3]=[CH:2]1.[CH3:12][Mg]Br.Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[O:1]1[C:5]2=[CH:6][N:7]=[C:8]([CH:10]([OH:11])[CH3:12])[CH:9]=[C:4]2[CH:3]=[CH:2]1
Under an argon atmosphere, furo[2,3-c]pyridine-5-carbaldehyde (488 mg, 3.31 mmol) was dissolved in tetrahydrofuran (11 mL), and added methylmagnesium bromide (5.5 mL (1.0 M in THF solution), 4.97 mmol) under ice-cold conditions. Then, the mixture was stirred at room temperature for 1.5 hours. The reaction solution was added 1N-aqueous solution of hydrochloric acid under ice-cold conditions, and then a saturated aqueous solution of sodium hydrogen carbonate was added. The reaction solution was extracted with ethyl acetate. The organic layer was 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 (356 mg (yield 66%)) was obtained as a yellow solid.
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