反应 #8209

反应方程式

NaH

2-(Trimethylsilylethynyl)-4,6-difluoro-N-carbethoxyaniline

ethyl acetate hexane

→

sodium ethoxide

5,7-difluoro-indole

收率 78.4%

溶剂

ethanol

ethanol

反应条件

后处理

1. 1
   其他reaction
2. 2
   其他is consumed
3. 3
   温度The mixture is heated
4. 4
   温度to reflux
5. 5
   其他is consumed (approx. 1 hour)
6. 6
   其他Reaction
7. 7
   浓缩concentrated
8. 8
   workup.ADDITIONdiethylether is added
9. 9
   洗涤washed with H2O, brine
10. 10
    干燥dried (Na2SO4)
11. 11
    过滤filtered
12. 12
    浓缩concentrated
13. 13
    其他is purified by flash chromatography (SiO2, ethyl acetate/hexane gradient)

实验过程

Fresh sodium ethoxide is prepared by carefully adding NaH (16 g of 60% oil dispersion, 400 mmol) to 550 mL of ethanol under N2. 2-(Trimethylsilylethynyl)-4,6-difluoro-N-carbethoxyaniline (28 g, 100 mmol) in 150 mL of ethanol is added and reaction is stirred at room temperature approximately 45 minutes, while monitoring by TLC (20% ethyl acetate/hexane, UV) until all the starting material is consumed. The mixture is heated to reflux and monitored by TLC until the intermediate material is consumed (approx. 1 hour). Reaction is cooled to room temperature, concentrated, diethylether is added, washed with H2O, brine, dried (Na2SO4), filtered, concentrated, and is purified by flash chromatography (SiO2, ethyl acetate/hexane gradient) to yield 12 g of 5,7-difluoro-indole (78%).

来源