Water → (2,2-Dimethyl-4-oxo-chroman-6-yl)boronic acid

HRID 1673846Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1673846
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([CH3:13])([CH3:12])[CH2:6][C:5]2=[O:14].[B:15]1(B2OC(C)(C)C(C)(C)O2)[O:19]C(C)(C)C(C)(C)[O:16]1.C([O-])(=O)C.[K+].O>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:12][C:7]1([CH3:13])[CH2:6][C:5](=[O:14])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([B:15]([OH:19])[OH:16])[CH:3]=2)[O:8]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 147553646-bromo-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one

Produkt 1

HCID 57460405(2,2-Dimethyl-4-oxo-chroman-6-yl)boronic acidAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 6-bromo-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one (21 g), pinacol diborane (25 g), palladium acetate (0.92 g) and potassium acetate (2.4 g) in N,N-dimethylformamide (250 mL) was stirred at 90° C. for 2 hr under an argon atmosphere. Water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in tetrahydrofuran (80 mL), and 0.5 M hydrochloric acid (40 mL) and sodium periodate (7.0 g) were added at 0° C. The reaction mixture was stirred at room temperature for 2 hr and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was crystallized from ethyl acetate and hexane to give the title compound (15 g, 84%) as a colorless solid.

Aufarbeitung

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in tetrahydrofuran (80 mL)
  6. addition0.5 M hydrochloric acid (40 mL) and sodium periodate (7.0 g) were added at 0° C
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. customThe residue was crystallized from ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-c911c876f8ac4ab59a3602500311b932
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07998968B2

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