[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:9]1[N:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:10]=1[C:11](OC)=[O:12])[CH3:8].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH2:7]([C:9]1[C:10]([CH2:11][OH:12])=[CH:15][CH:16]=[C:17]([CH3:19])[N:18]=1)[CH3:8]To a mixture of lithium aluminum hydride (220 mg) and THF (dry) (15 mL) was added a solution of methyl 2-ethyl-6-methylnicotinate (519 mg) in THF (dry) (5 mL) at 0° C. The mixture was stirred at 0° C. under nitrogen atmosphere for 20 min. To the mixture was added sodium sulfate decahydrate (1.8 g) and the mixture was stirred overnight. After filtrating, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (365 mg).
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