反应 #84515

反应方程式

diiodomethane

3-hydroxybenzonitrile

NaH

6-nitro-1H-indole

→

title compound

收率 51.0%

3-((6-nitro-1H-indol-1-yl)methoxy)benzonitrile

收率 51.0%

溶剂

DMF

DMF

DMF

DMF

反应条件

后处理

1. 1
   其他The mixture was then quenched with water
2. 2
   过滤filtered
3. 3
   萃取The filtrate was extracted with DCM (30 mL×6)
4. 4
   洗涤the combined organic layers were washed with brine (50 mL×3)
5. 5
   干燥dried over anhydrous Na2SO4
6. 6
   浓缩concentrated in vacuo
7. 7
   其他The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

实验过程

To a mixture of NaH (3.0 g, 75.0 mmol, 60%) in DMF (20 mL) were added a solution of 6-nitro-1H-indole (4.86 g, 30.0 mmol) in DMF (10 mL) and a solution of 3-hydroxybenzonitrile (3.57 g, 30.0 mmol) in DMF (10 mL) at 0° C. and the mixture was stirred at rt for 2 h. To the reaction mixture was added a solution of diiodomethane (7.5 mL, 90.0 mmol) in DMF (10 mL) slowly without light and the mixture was stirred at rt for 20 h. The mixture was then quenched with water and filtered. The filtrate was extracted with DCM (30 mL×6) and the combined organic layers were washed with brine (50 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a yellow solid (4.47 g, 51%).

来源