反应 #2171061

反应方程式

hydrochloric acid

3-acetyl-1-benzenesulfonyl-5-chloroindole

LHMDS

2-methoxybenzoylchloride

→

titled compound

收率 23.0%

1-(1-Benzenesulfonyl-5-chloroindol-3-yl)-3-(2-methoxyphenyl)-propan-1,3-dione

收率 23.0%

溶剂

water

THF

THF

反应条件

后处理

1. 1
   温度cooled again to −78° C
2. 2
   其他The reaction
3. 3
   温度mixyure was warmed to room temperature
4. 4
   萃取The mixture was extracted with ethyl acetate
5. 5
   洗涤washed with water
6. 6
   其他dried
7. 7
   其他The solvent was removed
8. 8
   其他the obtained residue was chromatographed on silica gel with ethyl acetate-n-hexane as eluent
9. 9
   浓缩The fraction of the objective was concentrated

实验过程

A solution of 500 mg (1.5 mmol) of 3-acetyl-1-benzenesulfonyl-5-chloroindole in THF (5 ml) was cooled it −78° C. Subsequently, to the reaction mixture was added 1.8 ml (1.8 mmol) of 1M LHMDS in THF. The solution was gradually warmed to 0° C. and cooled again to −78° C. To the solution was added 310 mg (1.8 mmol) of 2-methoxybenzoylchloride. The reaction mixyure was warmed to room temperature. After 30 minutes, the mixture was treated with water and acidified with 6 N hydrochloric acid. The mixture was extracted with ethyl acetate and washed with water, and then dried. The solvent was removed and the obtained residue was chromatographed on silica gel with ethyl acetate-n-hexane as eluent. The fraction of the objective was concentrated to give 160 mg of the titled compound as a foam. Yield: 23%.

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