反应 #2171060

反应方程式

3-acetyl-1-tert-butoxycarbonyl-indole

LHMDS

THF

THF

hydrochloric acid

phthalic anhydride

→

titled compound

收率 30.0%

1-(1-tert-Butoxycarbonyl-indol-3-yl)-3-(1-carboxyphenyl)-3-hydroxy-propen-1-one

收率 30.0%

反应条件

后处理

1. 1
   温度The mixture was cooled again to −78° C.
2. 2
   温度The reaction solution was warmed to room temperature
3. 3
   萃取extracted with ethyl acetate
4. 4
   洗涤The extract was washed with water
5. 5
   其他dried
6. 6
   浓缩concentrated
7. 7
   其他The obtained residue was crystallized from ethyl acetate-n-hexane

实验过程

To a solution of 777 mg (3 mmol) of 3-acetyl-1-tert-butoxycarbonyl-indole in THF (10 ml) was added 3.6 ml (3.6 mmol) of 1M LHMDS in THF at −78° C. The mixture was gradually warmed to room temperature. The mixture was cooled again to −78° C. and treated with 525 mg (3.6 mmol) of phthalic anhydride. The reaction solution was warmed to room temperature and mixed with ice water. The solution was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and dried, and then concentrated. The obtained residue was crystallized from ethyl acetate-n-hexane to give 362 mg of the titled compound. Yield: 30%.

来源