Реакция #302861

Уравнение реакции

boron tribromide

compound 25

6-methoxy-4′-dimethylaminoflavone

→

compound 27

6-hydroxy-4′-dimethylaminoflavone

Растворители

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   Температураunder cooling on ice
2. 2
   Другоеthe obtained mixture was then reacted
3. 3
   ДругоеAfter completion of the reaction
4. 4
   Другоеpurified water (100 ml)
5. 5
   workup.ADDITIONwas added to the reaction solution
6. 6
   Экстракцияthe dichloromethane layer was extracted
7. 7
   СушкаThe extract was dried over anhydrous sodium sulfate
8. 8
   workup.DISTILLATIONthe solvent was then distilled away under reduced pressure

Методика

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).

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