Reaktion #302861

Reaktionsgleichung

boron tribromide

compound 25

6-methoxy-4′-dimethylaminoflavone

→

compound 27

6-hydroxy-4′-dimethylaminoflavone

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder cooling on ice
2. 2
   Sonstigethe obtained mixture was then reacted
3. 3
   SonstigeAfter completion of the reaction
4. 4
   Sonstigepurified water (100 ml)
5. 5
   workup.ADDITIONwas added to the reaction solution
6. 6
   Extraktionthe dichloromethane layer was extracted
7. 7
   TrocknenThe extract was dried over anhydrous sodium sulfate
8. 8
   workup.DISTILLATIONthe solvent was then distilled away under reduced pressure

Vorschrift

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).

Quelle