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

HRID 2098961Notes

Reaction equation

HRID 2098961 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.Br[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CCOC(C)=O>CN(C=O)C>[CH2:13]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 2331475-Hydroxy-1-indanone

Product 1

HCID 107524065-(benzyloxy)-2,3-dihydro-1H-inden-1-oneYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-hydroxy-1-indanone 5.1 (available from Aldrich) (5 g, 34 mmol), 1-(bromomethyl)benzene (available from Aldrich) (4 mL, 37 mmol) and cesium carbonate (16 g, 51 mmol) in DMF (40 mL) was stirred at room temperature for 17 hours. EtOAc (400 mL) was added, and the mixture was washed with water and brine, and dried over anhydrous sodium sulfate. After removing solvent, the residue was purified by chromatography (silica gel, 1:4 EtOAc/hexane) to give 5.2 in 75% yield.

Workup

  1. washthe mixture was washed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customAfter removing solvent
  4. customthe residue was purified by chromatography (silica gel, 1:4 EtOAc/hexane)
  5. customto give 5.2 in 75% yield

Sources & evidence

ORD record
ord-0490c2fa5bd44cbdbd20b56098021b3f
Source dataset
uspto-grants-2013_05
Patent number
US08450522B2

Reaction notes

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