Hydrogen Peroxide → HCID 10420120, compound

HRID 2379817Notes

Reaction equation

HRID 2379817 reaction equation
OO.[C:3]([O:8][CH2:9][CH3:10])(=[O:7])[C:4]([CH3:6])=O.[C:11]([C:14]1C=C[N:17]=[CH:16][CH:15]=1)(=[O:13])[CH3:12].S(=O)(=O)(O)O>O.ClCCl>[C:11]([C:14]1[CH:15]=[CH:16][N:17]=[C:4]([C:3]([O:8][CH2:9][CH3:10])=[O:7])[CH:6]=1)(=[O:13])[CH3:12]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 12041Ethyl pyruvateHCID 142824-Acetylpyridine

Product 1

HCID 10420120HCID 10420120, compoundYield 24.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

30% Hydrogen peroxide (130 ml) was added to ethyl pyruvate (216 g) at -5° to 5° C. with stirring. This solution was then added to a mixture of 4-acetylpyridine (15.0 g), concentrated sulfuric acid (12.4 g), ferrous sulfate heptahydrate (345 g), dichloromethane (1.5 l) and water (100 ml) at the same temperature with stirring. After further stirring for 30 minutes, the resulting organic layer was separated. The solution was washed with aqueous sodium sulfite and then water, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography by eluting with a mixture of ethyl acetate and toluene (1:20) to give ethyl 4-acetyl-2-pyridinecarboxylate (5.79 g).

Workup

  1. stirringwith stirring
  2. stirringAfter further stirring for 30 minutes
  3. customthe resulting organic layer was separated
  4. washThe solution was washed with aqueous sodium sulfite
  5. dry with materialwater, dried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. washby eluting with a mixture of ethyl acetate and toluene (1:20)

Sources & evidence

ORD record
ord-5621fba2394443d498def04cc1afc5bf
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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