Potassium Carbonate → 3-(4-phenylbenzyloxy)-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene

HRID 1169323Notes

Reaction equation

HRID 1169323 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:20]1([C:26]2[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[C:20]1([C:26]2[CH:27]=[CH:28][C:29]([CH2:30][O:1][C:2]3[CH:13]=[CH:12][C:5]4[CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=4[CH:3]=3)=[CH:32][CH:33]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2295073-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-oneHCID 2577161,1'-Biphenyl, 4-(bromomethyl)-

Product 1

HCID 229899723-(4-phenylbenzyloxy)-5-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepteneYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3-hydroxy-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene (1.76 g, 10.0 mmol) dissolved in DMF (20 ml) were added potassium carbonate (2.76 g, 20.0 mmol) and 4-phenylbenzyl bromide (2.72 g, 11.0 mmol), and the resulting mixture was stirred at room temperature for 24 hours. The reaction mixture was concentrated under reduced pressure, ethyl acetate (30 ml) and THF (30 ml) were added to the residue and the resulting mixture was washed with water (10 ml, 5 ml×3) and an aqueous saturated solution of sodium chloride (5 ml). The organic layer was dried with anhydrous magnesium sulfate and was then concentrated under reduced pressure, and the residue was mixed with diisopropyl ether, and an insoluble material was collected by filtration. The insoluble material was washed with diisopropyl ether and was then dried under reduced pressure to obtain 3-(4-phenylbenzyloxy)-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene (3.00 g, 8.76 mmol, 88%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate (30 ml) and THF (30 ml)
  2. additionwere added to the residue
  3. washthe resulting mixture was washed with water (10 ml, 5 ml×3)
  4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  5. concentrationwas then concentrated under reduced pressure
  6. additionthe residue was mixed with diisopropyl ether
  7. filtrationan insoluble material was collected by filtration
  8. washThe insoluble material was washed with diisopropyl ether
  9. customwas then dried under reduced pressure

Sources & evidence

ORD record
ord-1285b46a02434a35adefbb331b2aed8a
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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