HCID 14277782, compound → HCID 14277772, compound

HRID 484019Notes

Reaction equation

HRID 484019 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([C:19]2S[CH:21]=[CH:22][CH:23]=2)[C:8]2[C:9](=[O:18])[C:10]([CH3:17])=[C:11]([CH3:16])[C:12](=[O:15])[C:13]=2[CH3:14])[CH:2]=1>C(O)C.[Ni]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([C:8]2[C:9](=[O:18])[C:10]([CH3:17])=[C:11]([CH3:16])[C:12](=[O:15])[C:13]=2[CH3:14])[CH2:19][CH2:23][CH2:22][CH3:21])[CH:2]=1

Participants

4

Reactant 1

HCID 14277782HCID 14277782, compound

Product 1

HCID 14277772HCID 14277772, compoundYield 72.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

The solution of 1.2 g (3.7 mmol) of 2-[(3-pyridyl)(2-thienyl)methyl]-3,5,6-trimethyl-1,4-benzoquinone in 20 ml of ethanol was refluxed by heating in the presence of 24 g of Raney nickel (W-6) for 5 hours. After cooling the catalyst was removed by filtration, and the filtrate was concentrated and redissolved in ethyl acetate and shaken with the solution of 1.2 g of ferric chloride in 10 ml of water. The mixture was made weakly alkaline with sodium hydrogen carbonate, from which the organic layer was separated, washed with water, dried, and concentrated. The residue was purified with silica gel column chromatography (ethyl acetate-isopropyl ether (1:1)), to give 0.8 g (72.5%) of 2-[1-(3-pyridyl)pentyl]-3,5,6-trimethyl-1,4-benzoquinone (Compound No. 7).

Workup

  1. temperatureAfter cooling the catalyst
  2. customwas removed by filtration
  3. concentrationthe filtrate was concentrated
  4. dissolutionredissolved in ethyl acetate
  5. customfrom which the organic layer was separated
  6. washwashed with water
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified with silica gel column chromatography (ethyl acetate-isopropyl ether (1:1))

Sources & evidence

ORD record
ord-149d78801666456a8b95f0d4b0d2d0d0
Source dataset
uspto-grants-1993_07
Patent number
US05229385

Reaction notes

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