反応 #792185

反応方程式

trimethylsilane

phenyl azide

1,1,4,7,7-pentamethyldiethlene triamine

TBAF

THF

→

4-(furan-2-yl)-1-phenyl-1H-1,2,3-triazole

収率 62.2%

反応条件

後処理

1. 1
   その他it was quenched with saturated ammonium chloride solution
2. 2
   抽出was extracted with ethyl acetate
3. 3
   洗浄The combined organic layers were washed with water
4. 4
   乾燥dried over anhydrous sodium sulfate
5. 5
   その他evaporated
6. 6
   その他The crude material was purified by column chromatography (100-200 mesh silica gel)

実験手順

To a solution of furan-2-ylethynyl)trimethylsilane (100 mg, 0.6097 mmol), phenyl azide (0.5 M solution, 2.42 ml, 1.2195 mmol), and CuI (116.11 mg, 0.6097 mmol) in THF (2 ml) was added 1,1,4,7,7-pentamethyldiethlene triamine (0.254 ml, 1.2195 mmol) and 1M TBAF.3H2O (1.20 ml, 1.2195 mmol). After stirring the reaction mixture for 20 hours at room temperature, it was quenched with saturated ammonium chloride solution and was extracted with ethyl acetate. The combined organic layers were washed with water, dried over anhydrous sodium sulfate and evaporated. The crude material was purified by column chromatography (100-200 mesh silica gel) using 5% ethyl acetate in hexane as eluent to yield 4-(furan-2-yl)-1-phenyl-1H-1,2,3-triazole (80 mg, 0.378 mmol, yield 62.18%) with an HPLC purity of 98.82%. LC-MS [M+H] 212 (C12H9N3O+H expected 212.07), mp 118-120° C. The 1H-NMR spectra was in accordance with the chemical structure.

出典