[H-].[Na+].[CH2:3]([O:5][C:6](=[O:13])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4].F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[C:17]([CH3:24])[CH:16]=1>CN(C)C=O>[CH2:3]([O:5][C:6](=[O:13])[CH:7]([C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[C:17]([CH3:24])[CH:16]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4]Sodium hydride (60% mineral oil; 0.599 g) was suspended in dimethylformamide (10 mL), and a solution of malonic acid diethyl ester (2.00 g) in dimethylformamide (10 mL) was added dropwise thereto under ice-cooling. After foam generation is stopped, a solution of 4-fluoro-2-methylnitrobenzene (1.94 g) in dimethylformamide (5 mL) was added thereto, and the reaction temperature was raised to 100° C., followed by stirring for 6 hours. The reaction mixture was concentrated, acidified with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel with ethyl acetate:hexane=1:5 to give the title compound (1.65 g) as a yellow oil.
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