反応 #88151

反応方程式

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

収率 33.4%

溶媒

water

DMSO

反応条件

後処理

1. 1
   温度The reaction was cooled
2. 2
   抽出extracted three times with EtOAc
3. 3
   乾燥The organic layers were dried over anhydrous sodium sulfate
4. 4
   ろ過filtered
5. 5
   その他Purification by flash chromatography (0-50% EtOAc/hexanes)

実験手順

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]+).

出典