Ethyl Acetate → HCID 22627651, compound

HRID 1384072Notes

Reaction equation

HRID 1384072 reaction equation
C(OC[C:6]1[O:7][C:8]2[C:14]([F:15])=[CH:13][CH:12]=[C:11]([F:16])[C:9]=2[CH:10]=1)(=O)C.C(=O)([O-])[O-:18].[K+].[K+].C(OCC)(=O)C>CO>[F:16][C:11]1[C:9]2[CH:10]=[C:6]([OH:18])[O:7][C:8]=2[C:14]([F:15])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 10632977HCID 10632977, compound

Product 1

HCID 22627651HCID 22627651, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 2-acetoxymethyl-4,7-difluorobenzofuran (252 mg) was dissolved in methanol (5 ml). After adding potassium carbonate (455 mg) at room temperature, the resulting mixture was stirred at the same temperature for 2 hr. Then ethyl acetate was added to the liquid reaction mixture and the organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: 5% ethyl acetate/n-hexane) to give 4,7-difluoro-2-hydroxybenzofuran (161 mg) as a colorless oil.

Workup

  1. washthe organic layer was washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (developing solvent: 5% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-469d1d279348436383b1a3657fed6079
Source dataset
uspto-grants-2001_07
Patent number
US06258811B1

Reaction notes

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