반응 #88151

반응 방정식

2-(4-(perfluoroethoxy)phenyl)-1,3,4-oxadiazole

methyl 4-iodobenzoate

1,10-phenanthroline

cesium carbonate

→

methyl 4-(5-(4-(perfluoroethoxy)phenyl)-1,3,4-oxadiazol-2-yl)benzoate

수율 33.4%

용매

water

DMSO

반응 조건

후처리

1. 1
   온도The reaction was cooled
2. 2
   추출extracted three times with EtOAc
3. 3
   건조The organic layers were dried over anhydrous sodium sulfate
4. 4
   여과filtered
5. 5
   기타Purification by flash chromatography (0-50% EtOAc/hexanes)

실험 절차

A mixture of 2-(4-(perfluoroethoxy)phenyl)-1,3,4-oxadiazole (2.186 g, 7.80 mmol), methyl 4-iodobenzoate (3.07 g, 11.70 mmol), copper(I) iodide (0.28 g, 1.47 mmol), 1,10-phenanthroline (0.30 g, 1.67 mmol), and cesium carbonate (2.54 g, 7.80 mmol) in anhydrous DMSO (20 mL) was heated at 100° C. for 18 hours. The reaction was cooled, diluted with water, and extracted three times with EtOAc. The organic layers were dried over anhydrous sodium sulfate, filtered, and adsorbed onto silica gel. Purification by flash chromatography (0-50% EtOAc/hexanes) provided methyl 4-(5-(4-(perfluoroethoxy)phenyl)-1,3,4-oxadiazol-2-yl)benzoate as a white solid (1.08 g, 33%): mp 185-191° C.; 1H NMR (400 MHz, CDCl3) δ 8.25-8.19 (m, 6H), 7.41 (t, J=9.4 Hz, 2H), 3.98 (s, 3H); 19F NMR (376 MHz, CDCl3) δ −85.96, −85.98, −87.79; ESIMS m/z 415 ([M+H]+).

출처