C1(C)C=CC(S([O:10][CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)(=O)=O)=CC=1.[OH:20][C:21]1[CH:26]=[C:25]([OH:27])[CH:24]=[CH:23][N:22]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[O:16]1[CH2:15][CH2:14][CH:13]([CH2:12][CH2:11][O:10][C:25]2[CH:24]=[CH:23][N:22]=[C:21]([OH:20])[CH:26]=2)[CH2:18][CH2:17]1.[O:16]1[CH2:15][CH2:14][CH:13]([CH2:12][CH2:11][O:10][C:21]2[CH:26]=[C:25]([OH:27])[CH:24]=[CH:23][N:22]=2)[CH2:18][CH2:17]1
To a solution of 2-(tetrahydro-2H-pyran-4-yl)ethyl p-toluenesulfonate (465 mg) in DMF (5 mL) were added 2,4-dihydroxypyridine (363 mg) and potassium carbonate (339 mg), and the mixture was stirred at 80° C. for 6 hours. The reaction mixture was allowed to cool to room temperature, and water (50 mL) was added thereto, followed by extraction with ethyl acetate (20 mL×3). The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: methanol/chloroform=0/100˜10/90) to obtain 4-[2-(tetrahydro-2H-pyran-4-yl)ethoxy]pyridin-2-ol (160 mg) as a major product, and 2-[2-(tetrahydro-2H-pyran-4-yl)ethoxy]pyridin-4-ol (Production Example 347) (43 mg) as a minor product.
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