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

HRID 980907Notes

Reaction equation

HRID 980907 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

4-(4-Pyridyl)cyclohex-3-enone ethyleneacetal (4 g) was dissolved in 70 ml of 0.5N hydrochloric acid. To the solution, there was added 400 mg of 10% palladium-carbon. Hydrogenation was carried out at room temperature under atmospheric pressure. After removing out the catalyst and adding an aqueous sodium hydroxide solution to alkalify, the reaction mixture was extracted with methylene chloride to obtain 2.7 g of 4-(4-pyridyl)cyclohexanone.

Workup

  1. customwas carried out at room temperature under atmospheric pressure
  2. customAfter removing out the catalyst
  3. additionadding an aqueous sodium hydroxide solution
  4. extractionthe reaction mixture was extracted with methylene chloride

Sources & evidence

ORD record
ord-0c1e7fc6cc3b428385c4721e4d91775d
Source dataset
uspto-grants-1987_01
Patent number
US04639521

Reaction notes

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