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

HRID 1699747Notes

Reaction equation

HRID 1699747 reaction equation
Br[C:2]1[C:10]2[O:11][CH2:12][CH2:13][C:9]=2[C:8]2[C:7](=[O:14])[CH2:6][CH2:5][C:4]=2[C:3]=1Br.C([O-])(=O)C.[Na+].O>CO.[Pd]>[CH2:13]1[CH2:12][O:11][C:10]2[CH:2]=[CH:3][C:4]3[CH2:5][CH2:6][C:7](=[O:14])[C:8]=3[C:9]1=2

Participants

6

Reactant 3

HCID 962WaterHCID 517045Sodium AcetateHCID 117272814,5-Dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one

Product 1

HCID 111376161,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-oneYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of 4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one (18.4 g, 55.4 mmols) in methanol (400 mL) was added 10% Palladium on activated carbon (2.0 g, 50% hydrous) followed by sodium acetate (12.6 g, 154 mmols). The mixture was stirred at 40° C. for 1.5 hours under hydrogen atmosphere (4 kgf/cm2). The catalyst was filtered off and the filtrate was concentrated under reduced pressure. Crystals were collected by filtration, washed with water and recrystallized successively with methanol:water=5:1 to obtain 8.0 g (yield: 83%) of the title compound.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. filtrationCrystals were collected by filtration
  4. washwashed with water
  5. customrecrystallized successively with methanol

Sources & evidence

ORD record
ord-8616af552c7f4501b2415e61120a90e8
Source dataset
uspto-grants-2002_02
Patent number
US06348485B1

Reaction notes

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