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

HRID 26686

반응식

HRID 26686 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 23938Palladium촉매2회HCID 180Acetone용매HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-15c03e503fec4509a2e2f164f7947f2d
출처 데이터셋
uspto-grants-1979_04
특허 번호
US04151179

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