Boron trifluoride etherate → Daidzein

HRID 418879

Reaktionsgleichung

Reaktionsgleichung von HRID 418879
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.B(F)(F)F.[CH3:23]COCC.CS(Cl)(=O)=O>CN(C=O)C>[OH:8][C:6]1[CH:7]=[C:2]2[C:3]([C:9](=[O:18])[C:10]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)=[CH:23][O:1]2)=[CH:4][CH:5]=1

Komponenten

5

Edukt 3

HCID 8000Boron trifluoride etherateHCID 31297Methanesulfonyl chlorideHCID 6400962,4,4'-Trihydroxydeoxybenzoin

Produkt 1

HCID 5281708Daidzein

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

In a solution of 1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)-ethanone (2 mmol) in DMF (6 mL), freshly distilled BF3.OEt2 (6.3 mL) was added under argon. The mixture was heated at 50° C., and a solution of methanesulphonyl chloride (1 mL) in dry DMF (1.5 mL) was added slowly. After reaction at 80° C. for 1 h, the mixture was cooled to rt and poured into a large volume of ice cold aq. sodium acetate (12 g/100 mL), then extracted with EtOAc, and the organic layer was dried and concentrated. The residue was purified by column chromatography on silica gel using a mixture of DCM and MeOH to give 7-hydroxy-3-(4-hydroxyphenyl)-chromen-4-one.

Aufarbeitung

  1. customAfter reaction at 80° C. for 1 h
  2. temperaturethe mixture was cooled to rt
  3. extractionextracted with EtOAc
  4. customthe organic layer was dried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel using
  7. additiona mixture of DCM and MeOH

Quellen und Nachweise

ORD-Eintrag
ord-3389877a413e4f5c9170966b8d4af98a
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093273B2

Verknüpfte Notizen

Wird geladen…