Water → HCID 23143496, compound

HRID 1437265Notes

Reaction equation

HRID 1437265 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)(=[O:3])[CH3:2].[C:10](OC)(=[O:15])[C:11]([O:13][CH3:14])=[O:12].C[O-].[Na+].O>CO>[CH3:14][O:13][C:11](=[O:12])[C:10](=[O:15])[CH2:2][C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11120Dimethyl oxalateHCID 142862-AcetylpyridineHCID 10942334Sodium Methoxide

Product 1

HCID 23143496HCID 23143496, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In an argon atmosphere at room temperature, 2-acetylpyridine (2.56 g) in methanol (26 mL) was added to dimethyl oxalate (5.00 g) and sodium methoxide (2.29 g) in methanol (26 mL), followed by stirring for 15 minutes. The mixture was stirred at 60° C. for 45 minutes, and then cooled in air. Water was added to the reaction mixture, and the resultant mixture was washed with diethyl ether. The aqueous layer was partitioned by use of saturated aqueous ammonium chloride and chloroform. The organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was removed under reduced pressure, to thereby give 4-(2-pyridyl)-2,4-dioxobutanoic acid methyl ester as a solid (3.44 g, 79%).

Workup

  1. stirringThe mixture was stirred at 60° C. for 45 minutes
  2. temperaturecooled in air
  3. washthe resultant mixture was washed with diethyl ether
  4. customThe aqueous layer was partitioned by use of saturated aqueous ammonium chloride and chloroform
  5. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  6. filtrationfollowed by filtration
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6a8c448584884057a921089891ddfdec
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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