Barium Sulfate → Methyl 2-[2,3-dihydro-2-ethyl-3-methyl-4-oxo-4H-1-benzopyran-6-yl]propionate

HRID 26686

Reaction equation

HRID 26686 reaction equation
[CH2:1]([C:3]1[O:4][C:5]2[CH:14]=[CH:13][C:12]([CH:15]([CH3:20])[C:16]([O:18][CH3:19])=[O:17])=[CH:11][C:6]=2[C:7](=[O:10])[C:8]=1[CH3:9])[CH3:2].S([O-])([O-])(=O)=O.[Ba+2].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>C(O)C.[Pd].CC(C)=O>[CH2:1]([CH:3]1[CH:8]([CH3:9])[C:7](=[O:10])[C:6]2[CH:11]=[C:12]([CH:15]([CH3:20])[C:16]([O:18][CH3:19])=[O:17])[CH:13]=[CH:14][C:5]=2[O:4]1)[CH3:2]

Participants

7

Reactant 3

HCID 24414Barium SulfateHCID 21322008Methyl 2-[2-ethyl-3-methyl-4-oxo-4H-1-benzopyran-6-yl]propionateHCID 131709961Jones' reagent

Product 1

HCID 21322013Methyl 2-[2,3-dihydro-2-ethyl-3-methyl-4-oxo-4H-1-benzopyran-6-yl]propionate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

Methyl 2-[2-ethyl-3-methyl-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 (0.49) 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-15c03e503fec4509a2e2f164f7947f2d
Source dataset
uspto-grants-1979_04
Patent number
US04151179

Linked notes

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