Water → 5-(benzyloxy)-2,3-dihydro-1H-inden-1-one

HRID 1163285Notes

Reaction equation

HRID 1163285 reaction equation
C(Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9](=[O:12])([O-])[O-].[K+].[K+].[C:15]([O:18][CH2:19][CH3:20])(=O)[CH3:16].O>CC(C)=O>[CH2:19]([O:18][C:15]1[CH:16]=[C:6]2[C:5](=[CH:4][CH:3]=1)[C:9](=[O:12])[CH2:2][CH2:7]2)[C:20]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate

Product 1

HCID 107524065-(benzyloxy)-2,3-dihydro-1H-inden-1-oneYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

This product was suspended in acetone (120 mL), and benzyl bromide (10.9 g, 64.0 mmol) and potassium carbonate (12.3 g, 88.9 mmol) were added, and the mixture was heated under reflux under nitrogen atmosphere for 1 hr. The reaction mixture was allowed to cool to room temperature, and ethyl acetate and water were added. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound (14.2 g, 94%) as pale-yellow crystals (recrystallized from ethyl acetate).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux under nitrogen atmosphere for 1 hr
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-70a73e11d62444fab929e9297538d358
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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