[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH2:10][CH2:11][OH:12].[H][H].[N+:15]([C:18]1[CH:23]=[CH:22][C:21](F)=[CH:20][CH:19]=1)([O-:17])=[O:16]>CN(C=O)C>[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([O:12][CH2:11][CH2:10][O:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=2)=[CH:20][CH:19]=1)([O-:17])=[O:16]To a suspension of sodium hydride (21.6 mg, 0.90 mmol) in anhydrous DMF (0.5 mL), 2-(pyridin-2-yloxy)-ethanol (100 mg, 0.72 mmol) in DMF (1.5 mL) was added drop-wise under a N2 atmosphere. Once hydrogen gas evolution ceased, 4-nitrofluorobenzene (102 mg, 0.72 mmol, 76 μL) was added drop-wise to the yellow suspension. The resultant red-orange solution was allowed to stir at rt for 18 h. Upon completion, distilled water (2 mL) was added and the bright yellow solid precipitate was filtered, washed with distilled water, and dried in vacuo to give 2-[2-(4-nitrophenoxy)ethoxy]pyridine as a pale yellow solid. 1H NMR (d6-DMSO, 400 MHz): δ 8.21 (ddd, J=5.6, 3.6, 3.6 Hz, 2H), 7.72 (ddd, J=9.2, 7.2, 2.0 Hz, 1H), 7.21 (ddd, J=5.6, 3.6, 3.6 Hz, 1H), 7.01 (ddd, J=7.0, 4.8, 0.8 Hz, 1H), 6.86 (ddd, J=8.4, 0.8, 0.8 Hz, 1H), 4.62 (m, 2H), 4.49 (m, 2H). MS(ES+): m/z 261 [MH+].
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