反応 #160837

反応方程式

Trichloracetyl chloride

aluminum trichloride

2-cyanopyrrole

→

desired product

収率 100.8%

4-(trichloroacetyl)-1H-pyrrole-2-carbonitrile

収率 100.8%

溶媒

ethyl acetate

dichloromethane

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   温度The reaction was heated
2. 2
   温度at reflux for 5 h
3. 3
   温度to cool
4. 4
   その他quenched slowly with water (300 mL)
5. 5
   その他The layers were separated
6. 6
   洗浄the organic layer was washed with water and brine
7. 7
   乾燥dried (magensium sulfate)
8. 8
   その他evaporated under reduced pressure

実験手順

Trichloracetyl chloride (44.4 g, 27.3 mL, 244 mmol) in dichloromethane (75 mL) was added over 20 min to a mechanically stirred suspension of aluminum trichloride (54.3 g, 407 mmol) in dichloromethane (150 mL). The resulting mixture was stirred for 30 min, and then 2-cyanopyrrole (15.0 g, 163 mmol) in dichloromethane (75 mL) was added over 30 min. The reaction was heated at reflux for 5 h and then allowed to cool. The reaction was diluted with ethyl acetate (600 mL) and then quenched slowly with water (300 mL). The layers were separated and then the organic layer was washed with water and brine, dried (magensium sulfate) and evaporated under reduced pressure to afford a quantitative yield of desired product (39.0 g, 100%) containing trace impurities. This material was used in the next step without further purification. 1H NMR (DMSO-d6) δ 8.14 (s, 1H), 7.55 (s, 1H).

出典