[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[C:9]([O:18][CH3:19])=[N:10][CH:11]=[C:12]([CH:17]=1)[C:13](OC)=[O:14].C(=O)([O-])O.[Na+]>O1CCCC1>[F:7][C:8]1[CH:17]=[C:12]([CH2:13][OH:14])[CH:11]=[N:10][C:9]=1[O:18][CH3:19]To a suspension of 0.24 g of lithium aluminum hydride in 6 mL of tetrahydrofuran, a solution of 0.58 g of methyl 5-fluoro-6-methoxynicotinate in 3.5 mL of tetrahydrofuran was dropped under cooling with ice. After warming to room temperature, the mixture was stirred for 30 minutes. Thereto was dropped a saturated aqueous sodium hydrogen carbonate solution under cooling with ice, after stirring for 10 minutes, the reaction mixture was filtered through celite, and the filtration residue was washed with ethyl acetate and water. The organic layer of the filtrate was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.55 g of (5-fluoro-6-methoxypyridin-3-yl)methanol as a brown oily substance.
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