Benzyl Bromide → 5-Benzyloxyadamantan-2-one

HRID 1515351Notes

Reaction equation

HRID 1515351 reaction equation
[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

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 64184Idramantone

Product 1

HCID 670177735-Benzyloxyadamantan-2-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3041555438694178a5c7fcd3df3613d0
Source dataset
uspto-grants-2012_07
Patent number
US08222417B2

Reaction notes

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