[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[C:17]([O:24][CH3:25])[CH:16]=1>CN(C)C=O.O>[CH3:25][O:24][C:17]1[CH:16]=[C:15]([CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10])[CH:20]=[CH:19][C:18]=1[N+:21]([O-:23])=[O:22]To a suspension of NaH (151 g, 88 mmol) in dry N,N-dimethylformamide (40 mL) at 0° C. was added diethyl malonate (10.3 g, 64.3 mmol) and the mixture was stirred at room temperature for 30 minutes. A solution of 4-fluoro-2-methoxy-1-nitrobenzene (10 g, 58.5 mmol) was added and the mixture was stirred at 90° C. overnight. The mixture was diluted with water and extracted with ethyl acetate (3×20 mL). The combined organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel eluting with a gradient of 1/20 to 1/10 ethyl acetate/petroleum ether to afford the title compound.
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