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Ethyl-2-[2-(1,1-dimethylethyl)-4-oxo-4H-1-benzopyran-6-yl]propionate → Ethyl-2-[2,3-dihydro-2-(1,1-dimethylethyl)-4-oxo-4H-1-benzopyran-6-yl]propionate

HRID 26681
Notes
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Reaction equation

HRID 26681 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH:5]([C:7]1[CH:8]=[CH:9][C:10]2[O:15][C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:13][C:12](=[O:20])[C:11]=2[CH:21]=1)[CH3:6])[CH3:2].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>C(O)C.[Pd].CC(C)=O>[CH2:1]([O:3][C:4](=[O:22])[CH:5]([C:7]1[CH:8]=[CH:9][C:10]2[O:15][CH:14]([C:16]([CH3:18])([CH3:17])[CH3:19])[CH2:13][C:12](=[O:20])[C:11]=2[CH:21]=1)[CH3:6])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 54572468Ethyl-2-[2-(1,1-dimethylethyl)-4-oxo-4H-1-benzopyran-6-yl]propionateHCID 131709961Jones' reagent

Product 1

HCID 54545077Ethyl-2-[2,3-dihydro-2-(1,1-dimethylethyl)-4-oxo-4H-1-benzopyran-6-yl]propionate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 180AcetoneSolvent
HCID 702EthanolSolvent

Procedure

Ethyl-2-[2-(1,1-dimethylethyl)-4-oxo-4H-1-benzopyran-6-yl]propionate (6.61 g) was taken up in dry ethanol (150 ml) and hydrogenated at 85 p.s.i. with 5% palladium on carbon (0.2 g) and 5% palladium on barium sulphate (0.4 g) for a total of 48 hours. The catalyst was removed by filtration (`Hyflo` supercel) and the ethanol removed in vacuo affording an oil. The oil was taken up in acetone (50 ml) and treated with a slight excess of Jones reagent. The excess oxidant was destroyed with methanol and the reaction mixture was dissolved in water (200 ml) and extracted with ether. The combined ethereal extracts were washed with water, dilute aqueous sodium bicarbonate solution and water, dried (MgSO4) and concentrated in vacuo to give the title compound as an oil - 6 g.

Workup

  1. customfor a total of 48 hours
  2. customThe catalyst was removed by filtration (`Hyflo` supercel) and the ethanol
  3. customremoved in vacuo
  4. customaffording an oil
  5. customThe excess oxidant was destroyed with methanol
  6. dissolutionthe reaction mixture was dissolved in water (200 ml)
  7. extractionextracted with ether
  8. washThe combined ethereal extracts were washed with water, dilute aqueous sodium bicarbonate solution and water
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ac8f4a81e1dd4b7caa6ee912ad10f7ca
Source dataset
uspto-grants-1979_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04151179

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes