Sodium Bicarbonate → 5-(3,5,6-Trimethyl-1,4-benzoquinon-2-yl)-5-(3-pyridyl)pentanoic acid

HRID 484015Notes

Reaction equation

HRID 484015 reaction equation
C[O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11]C)=[C:5]([CH3:13])[C:4]=1[CH:14]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19].[N+]([O-])([O-])=O.[NH4+].[Ce].C(=O)([O-])O.[Na+]>C(#N)C.O>[CH3:13][C:5]1[C:6](=[O:11])[C:7]([CH3:10])=[C:8]([CH3:9])[C:3](=[O:2])[C:4]=1[CH:14]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 145762585-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-5-(3-pyridyl)pentanoic acidHCID 57418452Ammonium cerium-nitrate

Product 1

HCID 142777715-(3,5,6-Trimethyl-1,4-benzoquinon-2-yl)-5-(3-pyridyl)pentanoic acidYield 54.5%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent2×

Procedure

The solution of 400 mg (1.12 mmol) of 5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-5-(3-pyridyl)pentanoic acid in 8 ml of acetonitrile-water (1:1) was cooled to 0° C., to which the solution of 1.55 g (2.82 mmol) of cerium ammonium nitrate in 6 ml of acetonitrile-water (1:1) was added with stirring. The reaction mixture was stirred for 30 minutes, neutralized with sodium hydrogen carbonate, and extracted with ethyl acetate. The extract was washed with water and dried, and the solvent was evaporated off. The residue was purified with silica gel column (ethyl acetate), and recrystallized from ethanol, to give 200 mg (54.3%) of 5-(3,5,6-trimethyl-1,4-benzoquinon -2-yl)-5-(3-pyridyl)pentanoic acid.

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred for 30 minutes
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. customthe solvent was evaporated off
  7. customThe residue was purified with silica gel column (ethyl acetate)
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-364cb076e21b4585b11d275895ac763c
Source dataset
uspto-grants-1993_07
Patent number
US05229385

Reaction notes

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