반응 #302861

반응 방정식

boron tribromide

compound 25

6-methoxy-4′-dimethylaminoflavone

→

compound 27

6-hydroxy-4′-dimethylaminoflavone

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   온도under cooling on ice
2. 2
   기타the obtained mixture was then reacted
3. 3
   기타After completion of the reaction
4. 4
   기타purified water (100 ml)
5. 5
   workup.ADDITIONwas added to the reaction solution
6. 6
   추출the dichloromethane layer was extracted
7. 7
   건조The extract was dried over anhydrous sodium sulfate
8. 8
   workup.DISTILLATIONthe solvent was then distilled away under reduced pressure

실험 절차

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).

출처