反应 #302861

反应方程式

boron tribromide

compound 25

6-methoxy-4′-dimethylaminoflavone

→

compound 27

6-hydroxy-4′-dimethylaminoflavone

溶剂

dichloromethane

dichloromethane

反应条件

后处理

1. 1
   温度under cooling on ice
2. 2
   其他the obtained mixture was then reacted
3. 3
   其他After completion of the reaction
4. 4
   其他purified water (100 ml)
5. 5
   workup.ADDITIONwas added to the reaction solution
6. 6
   萃取the dichloromethane layer was extracted
7. 7
   干燥The extract was dried over anhydrous sodium sulfate
8. 8
   workup.DISTILLATIONthe solvent was then distilled away under reduced pressure

实验过程

A dichloromethane solution (5 ml) that contained boron tribromide was slowly added to a dichloromethane solution (50 ml) that contained compound 25 (200 mg, 0.68 mmol) while stirring under cooling on ice, and the obtained mixture was then reacted. After completion of the reaction, purified water (100 ml) was added to the reaction solution, and the dichloromethane layer was extracted. The extract was dried over anhydrous sodium sulfate, and the solvent was then distilled away under reduced pressure. The residue was subjected to silica gel column chromatography using chloroform/methanol (20/1) as an elution solvent, so as to obtain a product of interest, 6-hydroxy-4′-dimethylaminoflavone (compound 27). Yield: 25 mg (yield constant: 13.1%) 1H NMR (300 MHz, DMSO-d6) δ 9.94 (s, 1H), 7.90 (d, J=9.0 Hz, 2H), 7.30 (m, 1H), 7.19-7.22 (m, 1H), 6.82 (d, J=9.0 Hz, 2H), 6.73 (s, 1H), 3.03 (s, 6H).

来源