反応 #7051

反応方程式

bromoacetonitrile

7-hydroxy-1H-indole

potassium carbonate

→

(1H-Indol-7-yloxy)-acetonitrile

溶媒

acetonitrile

反応条件

後処理

1. 1
   その他In a 100 mL roundbottom flask equipped with a magnetic stirrer
2. 2
   温度to warm to ambient temperature
3. 3
   workup.STIRRINGstirring
4. 4
   洗浄The solution was washed with water (2×30 mL) and brine (1×30 mL)
5. 5
   乾燥dried over MgSO4
6. 6
   濃縮concentrated in vacuo
7. 7
   その他The resulting oily brown residue was purified by flash chromatography (95:5 ethyl acetate:hexanes to 85:15 ethyl acetate:hexanes over minutes)

実験手順

In a 100 mL roundbottom flask equipped with a magnetic stirrer and rubber septum, 7-hydroxy-1H-indole (1.66 g., 12.48 mmol) was dissolved 50 mL anhydrous acetonitrile. The flask was charged with potassium carbonate (6.88 g., 49.9 mmol) and cooled to 0° C. While stirring, bromoacetonitrile (1.64 g., 13.73 mmol) was added dropwise over two minutes. The reaction mixture was allowed to warm to ambient temperature and stirring was continued for three hours. The solution was washed with water (2×30 mL) and brine (1×30 mL), dried over MgSO4 and concentrated in vacuo. The resulting oily brown residue was purified by flash chromatography (95:5 ethyl acetate:hexanes to 85:15 ethyl acetate:hexanes over minutes) to give (1H-Indol-7-yloxy)-acetonitrile as a crystalline solid (0.244-g.) ms: (M−H)−=171.2.

出典