Water → 1-(4-Methoxy-2-benzofuranyl)-1,3-butanedione

HRID 2085163Notes

Reaction equation

HRID 2085163 reaction equation
[C:1]([C:4]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH3:14])[C:6]=2[CH:5]=1)(=[O:3])[CH3:2].[H-].[Na+].O.[C:18](OCC)(=[O:20])[CH3:19]>>[CH3:14][O:13][C:12]1[C:6]2[CH:5]=[C:4]([C:1](=[O:3])[CH2:2][C:18](=[O:20])[CH3:19])[O:8][C:7]=2[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 3042306Ethanone, 1-(4-methoxy-2-benzofuranyl)-

Product 1

HCID 227289761-(4-Methoxy-2-benzofuranyl)-1,3-butanedione

Procedure

2-Acetyl-4-methoxybenzo(b)furan (2.4 g) was dissolved in ethyl acetate (50 ml), and sodium hydride (1.5 g) was added under ice-cooling. The mixture was stirred at room temperature for 10 min, and the mixture was refluxed under heating for 1 hr. After cooling, the mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and after filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (0.7 g).

Workup

  1. temperaturecooling
  2. temperaturethe mixture was refluxed
  3. temperatureunder heating for 1 hr
  4. temperatureAfter cooling
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationafter filtration
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-968c8718b59d40ed9865d36c8785c6c7
Source dataset
uspto-grants-2004_04
Patent number
US06720320B2

Reaction notes

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