Water → HCID 14044829, compound

HRID 494917Notes

Reaction equation

HRID 494917 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[CH:20]=[CH2:21].O>CN(C)C=O.C(OCC)(=O)C>[CH2:21]([O:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11])[CH:20]=[CH2:19]

Participants

7

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11092PaeonolHCID 11430Potassium Carbonate

Product 1

HCID 14044829HCID 14044829, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5.00 g of 2′-hydroxy-4′-methoxyacetophenone was dissolved in 40 ml of N,N-dimethylformamide at room temperature. Thereafter, 4.16 g of potassium carbonate and 2.80 ml of allyl bromide were successively added to the reaction solution. After the disappearance of materials had been confirmed, water and ethyl acetate were added to the reaction solution, so as to separate an organic layer. The obtained organic layer was washed with water and a saturated sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure, and the residue was then purified by silica gel column chromatography (hexane/ethyl acetate), so as to obtain 5.60 g of the subject compound.

Workup

  1. customso as to separate an organic layer
  2. washThe obtained organic layer was washed with water
  3. dry with materiala saturated sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate
  4. customAfter removing the drying agent
  5. filtrationby filtration
  6. concentrationthe organic layer was concentrated under a reduced pressure
  7. customthe residue was then purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f5a47944179a41319aa57db2cd9ce14a
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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