[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9](OC)=[O:10])[CH:6]=[CH:5][CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>CCOCC>[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=1To methyl 6-methoxypicolinate (4.65 g, 27.8 mmol) in Et2O (100 mL) was added LAH (1.06 g). The reaction mixture was stirred for 4 hours. Celite (10 g) was added, followed by sodium sulfate-decahydrate (5 g). The reaction mixture was filtered and concentrated to provide the desired product (3.36 g).
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