Benzyl Bromide → 5-Benzyloxyadamantan-2-one

HRID 1515351

Reaktionsgleichung

Reaktionsgleichung von HRID 1515351
[O:1]=[C:2]1[CH:9]2[CH2:10][C:5]3([OH:12])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O.[Cl-].[NH4+]>[CH2:15]([O:12][C:5]12[CH2:4][CH:3]3[CH2:11][CH:7]([CH2:8][CH:9]([C:2]3=[O:1])[CH2:10]1)[CH2:6]2)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 64184Idramantone

Produkt 1

HCID 670177735-Benzyloxyadamantan-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

To a solution of 4-oxoadamantan-1-ol (5.0 g) in N,N-dimethylformamide (50 ml), sodium hydride (60%, 1.4 g) and benzyl bromide (3.9 ml) were added under ice cooling. The reaction mixture was then warmed to room temperature and stirred for 1 hour. The reaction mixture was diluted with saturated aqueous ammonium chloride under ice cooling and extracted with ethyl acetate. The extracted organic layer was washed with brine, dried over anhydrous magnesium sulfate and then filtered to remove the desiccant, followed by distilling off the solvent under reduced pressure to give 5-benzyloxyadamantan-2-one (8g) as a colorless oil.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extracted organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customto remove the desiccant
  6. distillationby distilling off the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3041555438694178a5c7fcd3df3613d0
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222417B2

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