HCID 54512700, compound → HCID 14277778, compound

HRID 232064Notes

Reaction equation

HRID 232064 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([C:16]2[C:17](=[O:26])[C:18]([CH3:25])=[C:19]([CH3:24])[C:20](=[O:23])[C:21]=2[CH3:22])=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH:2]=1>C(O)(=O)C.[C].[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([C:16]2[C:17](=[O:26])[C:18]([CH3:25])=[C:19]([CH3:24])[C:20](=[O:23])[C:21]=2[CH3:22])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH:2]=1

Participants

4

Reactant 1

HCID 54512700HCID 54512700, compound

Product 1

HCID 14277778HCID 14277778, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

7-(3-pyridyl)-7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-6-heptenoic acid (2.5 g) was hydrogenated in the presence of 5% palladium-carbon (0.5 g) in acetic acid (20 ml) (the reaction completed in about 2 hours). The catalyst was removed, the solvent was concentrated, and water (10 ml) and methanol (40 ml) were added. This solution was neutralized by addition of a saturated solution of sodium hydrogen carbonate, and the hydroquinone derivative was oxidized by aeration. After completion of oxidation, the mixture was concentrated under reduced pressure and the product was extracted with chloroform. The organic phase was dried with magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in ethyl acetate and purified with silica gel column chromatography [ethyl acetate-ethanol(9:1)] and recrystallized from a mixture of ethyl acetate-isopropyl ether, to give 7-(3-pyridyl)-7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)heptanoic acid (2.1 g).

Workup

  1. customThe catalyst was removed
  2. concentrationthe solvent was concentrated
  3. additionwater (10 ml) and methanol (40 ml) were added
  4. additionThis solution was neutralized by addition of a saturated solution of sodium hydrogen carbonate
  5. concentrationAfter completion of oxidation, the mixture was concentrated under reduced pressure
  6. extractionthe product was extracted with chloroform
  7. dry with materialThe organic phase was dried with magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. dissolutionThe residue was dissolved in ethyl acetate
  10. custompurified with silica gel column chromatography [ethyl acetate-ethanol(9:1)]
  11. customrecrystallized from a mixture of ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-51332211ea9641baa445b9be6c8e8306
Source dataset
uspto-grants-1989_07
Patent number
US04851413

Reaction notes

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