4,4-Dimethyl-1-(3-pyridinyl)-1-penten-3-one → HCID 4547109, compound

HRID 443842Notes

Reaction equation

HRID 443842 reaction equation
[CH3:1][C:2]([CH3:14])([CH3:13])[C:3](=[O:12])[CH:4]=[CH:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1>O1CCCC1.[Ni]>[CH3:1][C:2]([CH3:14])([CH3:13])[C:3](=[O:12])[CH2:4][CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 536634384,4-Dimethyl-1-(3-pyridinyl)-1-penten-3-one

Product 1

HCID 4547109HCID 4547109, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

154.2 g (0.814 mol) of 4,4-dimethyl-1-pyridin-3-yl-1-penten-3-one were dissolved in 750 ml of tetrahydrofuran and the solution was stirred with about 20 g of Raney nickel. The solution was filtered, a further 20 g of Raney nickel were added and hydrogenation was carried out under the usual pressure and at room temperature until, according to the thin layer chromatogram, no further starting material was present. The Raney nickel was filtered off from the solution, the filtrate was concentrated and the residue was distilled. 119.8 g (78% of theory) Of 4,4-dimethyl-1-pyridin-3-yl-pentan-3-one of boiling point 123°-130° C./2.3 mm Hg were obtained. ##STR118##

Workup

  1. filtrationThe solution was filtered
  2. additiona further 20 g of Raney nickel were added
  3. customwas carried out under the usual pressure and at room temperature
  4. filtrationThe Raney nickel was filtered off from the solution
  5. concentrationthe filtrate was concentrated
  6. distillationthe residue was distilled

Sources & evidence

ORD record
ord-4239a6db0ee4452a9bcb9babe8e8a893
Source dataset
uspto-grants-1981_04
Patent number
US04262000

Reaction notes

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