4-(3-Pyridyl)cyclohex-3-en-1-one ethylene acetal → 4-(3-Pyridyl)cyclohexanone ethylene acetal

HRID 475698Notes

Reaction equation

HRID 475698 reaction equation
[CH2:1]1[O:16][C:4]2([CH2:9][CH2:8][C:7]([C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)=[CH:6][CH2:5]2)[O:3][CH2:2]1>CCOC(C)=O.[Pd]>[CH2:2]1[O:3][C:4]2([CH2:5][CH2:6][CH:7]([C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)[CH2:8][CH2:9]2)[O:16][CH2:1]1

Participants

4

Reactant 1

HCID 200349034-(3-Pyridyl)cyclohex-3-en-1-one ethylene acetal

Product 1

HCID 578925504-(3-Pyridyl)cyclohexanone ethylene acetal

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(3-pyridyl)cyclohex-3-en-1-one ethylene ketal prepared above (26 g, 120.0 mmol) in EtOAc (240 mL), containing 10% Pd/C (3.9 g), was hydrogenated under atmospheric pressure for 24 h. At this time, an additional 1.3 g of 10% Pd/C was added and the mixture allowed to stir an additional 2.5 d under an atmosphere of hydrogen gas. The reaction mixture was filtered through a pad of celite and concentrated in vacuo to afford crude 4-(3-pyridyl)cyclohexanone ethylene ketal, which was used without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-51da6f8b9e4144cba235f189bfe33866
Source dataset
uspto-grants-2014_01
Patent number
US08637576B2

Reaction notes

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