Potassium Carbonate → Ethyl (2-acetyl-4-fluorophenoxy)acetate

HRID 1582754Notes

Reaction equation

HRID 1582754 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.I[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][O:11][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][C:6]=1[C:8](=[O:10])[CH3:9])[CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12183Ethyl iodoacetateHCID 959922-Acetyl-4-fluorophenol

Product 1

HCID 22718336Ethyl (2-acetyl-4-fluorophenoxy)acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5′-Fluoro-2′-hydroxyacetophenone 2.0 g, ethyl iodoacetate 4.16 g and potassium carbonate 2.7 g were added to acetone 43 ml in a nitrogen atmosphere, and the mixture was stirred overnight under reflux with heating. After cooled to room temperature, the potassium carbonate was filtered off through Celite, and the filtrate was partitioned by adding water and ethyl acetate. The organic layer was washed with water and then with brine, dried over magnesium sulfate anhydride, and evaporated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate system), whereby the title compound 3.07 g, 99% was obtained as a colorless oil.

Workup

  1. temperatureunder reflux
  2. temperaturewith heating
  3. filtrationthe potassium carbonate was filtered off through Celite
  4. customthe filtrate was partitioned
  5. additionby adding water and ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialwith brine, dried over magnesium sulfate anhydride
  8. customevaporated
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate system), whereby the title compound 3.07 g, 99%
  10. customwas obtained as a colorless oil

Sources & evidence

ORD record
ord-dacc81cb9c9342508ac19aab38d403d4
Source dataset
uspto-grants-2004_05
Patent number
US06737425B1

Reaction notes

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