[N:1]1[CH:6]=[CH:5][C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:3][C:2]=1[C:11](OC)=[O:12].[H-].C([Al+]CC(C)C)C(C)C.C(OCC)C.CCCCCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH:11]([C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][N:1]=1)[C:7]([O:9][CH3:10])=[O:8])=[O:12]
1.07 g of dimethyl pyridine-2,4-dicarboxylate was dissolved in 20 ml of toluene, and with stirring under cooling at -80° to -70° C., 6.04 ml of a 1M toluene solution of diisobutylaluminium hydride was added dropwise over 2.5 hours, and the mixture was stirred at this temperature for 1 hour. The reaction mixture was poured into ice water, and ethyl ether was added. The organic layer was separated, worked up in a customary manner, and then purified by medium-pressure liquid chromatography Lobar column, size B, Lichroprep Si 60 (E. Merck Co.); eluting solvent: hexane/ethyl acetate=4/1→3/1) to give 0.27 g (yield 30%) of methyl 2-formylisonicotinate as a colorless crystalline powder.
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