反应 #2271703

反应方程式

1-bromo-3-chloropropane

sodium hydride

7-hydroxyindole

water

→

7-(3-chloropropoxy)indole

溶剂

dimethylformamide

dimethylformamide

dimethylformamide

反应条件

后处理

1. 1
   workup.ADDITIONAfter complete addition
2. 2
   温度cooled to 15° C
3. 3
   workup.ADDITIONTo this cooled solution was added
4. 4
   workup.STIRRINGThe reaction was then stirred at ambient temperature for 16 hours
5. 5
   萃取the aqueous suspension extracted with ethyl acetate
6. 6
   洗涤The ethyl acetate was washed with water
7. 7
   干燥dried (MgSO4)
8. 8
   浓缩the solvent was concentrated
9. 9
   其他to afford a dark brown oil

实验过程

To a stirred suspension of sodium hydride (0.8 g, 17 mmol of a 50% oil dispersion in dimethylformamide (20 ml), under nitrogen, was added dropwise 7-hydroxyindole (2.1 g, 15.7 mmol) in dimethylformamide (20 ml). After complete addition, the reaction was stirred at ambient temperature for 0.5 hour and then cooled to 15° C. To this cooled solution was added, dropwise, 1-bromo-3-chloropropane (2.5 g, 15.7 mmol) in dimethylformamide (5 ml). The reaction was then stirred at ambient temperature for 16 hours. The reaction was poured into water, and the aqueous suspension extracted with ethyl acetate. The ethyl acetate was washed with water, dried (MgSO4), and the solvent was concentrated to afford a dark brown oil. Following flash chromatography an silica gel. 7-(3-chloropropoxy)indole was obtained as a colorless oil, 1.0 g. ANALYSIS: Calculated for C11H12ClNO: 63.01%C 5.77%H 6.68%,N Found: 63.25%C 5.61%H 6.65%N

来源