Sodium Acetate → 1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one

HRID 324616Notes

Reaction equation

HRID 324616 reaction equation
C([O-])(=O)C.[Na+].Br[C:7]1[C:15]2[O:16][CH2:17][CH2:18][C:14]=2[C:13]2[C:12](=[O:19])[CH2:11][CH2:10][C:9]=2[C:8]=1Br.[H][H]>C(O)(=O)C.[C].[Pd]>[CH2:18]1[CH2:17][O:16][C:15]2[CH:7]=[CH:8][C:9]3[CH2:10][CH2:11][C:12](=[O:19])[C:13]=3[C:14]1=2

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 117272814,5-Dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 111376161,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

5% Palladium carbon (50% hydrous, 2.9 g) and sodium acetate (17.9 g, 0.22 mol) were added to a solution of 4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one (29.0 g, 87.4 mmol) in acetic acid (550 ml), and the mixture was catalytically reduced in a hydrogen atmosphere at ordinary temperature and ordinary pressure. After absorption of the calculated amount of hydrogen, the palladium carbon was filtered off and the solvent was distilled off under reduced pressure. Water was added to the residue and the organic matter was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium bicarbonate solution, a saturated aqueous sodium chloride solution and water and then dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue obtained was purified by silica gel column chromatogarphy (ethyl acetate:hexane=15:85) to give the target compound. The yield was 13.5 g (89%).

Workup

  1. customAfter absorption of the calculated amount of hydrogen
  2. filtrationthe palladium carbon was filtered off
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionWater was added to the residue
  5. extractionthe organic matter was extracted with ethyl acetate
  6. washThe extract was washed with a saturated aqueous sodium bicarbonate solution
  7. dry with materiala saturated aqueous sodium chloride solution and water and then dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue obtained
  10. customwas purified by silica gel column chromatogarphy (ethyl acetate:hexane=15:85)
  11. customto give the target compound

Sources & evidence

ORD record
ord-5c49d59ab6644dfda6595af99d4ac77f
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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