反応 #84515

反応方程式

diiodomethane

3-hydroxybenzonitrile

NaH

6-nitro-1H-indole

→

title compound

収率 51.0%

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

収率 51.0%

溶媒

DMF

DMF

DMF

DMF

反応条件

後処理

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

実験手順

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%).

出典