[CH3:1][C:2]1[O:3][C:4]([CH3:10])=[C:5]([CH2:7][CH2:8][OH:9])[N:6]=1.F[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1.[H-].[Na+].O>CN(C)C=O>[CH3:1][C:2]1[O:3][C:4]([CH3:10])=[C:5]([CH2:7][CH2:8][O:9][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[N:6]=12-(2,5-Dimethyl-4-oxazolyl)ethanol (17.0 g) and 4-fluoronitrobenzene (17.0 g) were dissolved in N,N-dimethylformamide (150 ml), and 60% sodium hydride in oil (6.0 g) was added dropwise to the solution under vigorous stirring. After stirring at room temperature for 1 hour, the reaction mixture was poured into water (1 l) and the crystals which separated out were collected by filtration and recrystallized from ethyl acetate-hexane to give 4-[2-(2,5-dimethyl-4-oxazolyl)ethoxy]nitrobenzene (27.5 g. 87.0%). Colorless columns, m.p. 97°-98° C. Elemental analysis for C13H14N2O4, Calcd.: C, 59.94; H, 5.38; N, 10.68. Found: C, 59.72; H, 5.44; N, 10.63.
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