4-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)pyridine → Cyclohexanone, 4-(4-pyridinyl)-

HRID 231217Notes

Reaction equation

HRID 231217 reaction equation
C1O[C:4]2([CH2:9][CH2:8][C:7]([C:10]3[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=3)=[CH:6][CH2:5]2)[O:3]C1>Cl.[C].[Pd]>[N:13]1[CH:14]=[CH:15][C:10]([CH:7]2[CH2:6][CH2:5][C:4](=[O:3])[CH2:9][CH2:8]2)=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 137720544-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)pyridine

Product 1

HCID 10154273Cyclohexanone, 4-(4-pyridinyl)-Yield 83.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 313Hydrochloric AcidSolvent

Procedure

In 70 ml of 0.5N hydrochloric acid was dissolved 4 g of 4-(4-pyridyl)cyclohex-3-enone ethyleneacetal and, 400 mg of 10% palladium-carbon was added to the solution followed by hydrogenation at normal temperature under normal pressure. After completion of the reaction, the catalyst was removed. After the system was rendered alkaline with a sodium hydroxide aqueous solution, it was extracted with methylene chloride to give 2.7 g of 4-(4-pyridyl)cyclohexanone.

Workup

  1. additionwas added to the solution
  2. customAfter completion of the reaction
  3. customthe catalyst was removed
  4. extractionwas extracted with methylene chloride

Sources & evidence

ORD record
ord-9062c33e34f0478e821659a29094c4d9
Source dataset
uspto-grants-1989_07
Patent number
US04845228

Reaction notes

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