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

HRID 621707Notes

Reaction equation

HRID 621707 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.[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 23938PalladiumCatalystHCID 313Hydrochloric AcidSolvent

Procedure

4 g of 4-(4-pyridyl)cyclohex-3-enone ethylene acetal was dissolved in 70 ml of 0.5 N hydrochloric acid and 400 mg of 10% palladium/carbon was added thereto, to hydrogenate the starting compound at room temperature and atmospheric pressure. After the completion of the reaction, the catalyst was removed and the reaction mixture was made alkaline with an aqueous solution of sodium hydroxide and extracted with methylene chloride to thereby give 2.7 g of 4-(4-pyridyl)cyclohexanone. NMRδTMSCDCl3 : 1.7-2.3 (4H, m), 2.4-2.6 (4H, m), 2.8-3.2 (1H, M), 7.15 (2H, d) and 8.51 (2H, m).

Workup

  1. customat room temperature
  2. customAfter the completion of the reaction
  3. customthe catalyst was removed
  4. extractionextracted with methylene chloride

Sources & evidence

ORD record
ord-0c711860ed1940e1aba5f2381a9d7578
Source dataset
uspto-grants-1989_04
Patent number
US04824952

Reaction notes

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