Water → Ethyl 4-(4-methyl-2-pyridyl)-2,4-dioxobutanoate

HRID 1437274Notes

Reaction equation

HRID 1437274 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2]([O:4]CC)=O.[O-]CC.[Na+].[CH3:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22](=[O:24])[CH3:23])[CH:17]=1.O>C(O)C>[CH2:9]([O:8][C:1](=[O:7])[C:2](=[O:4])[CH2:23][C:22]([C:18]1[CH:17]=[C:16]([CH3:15])[CH:21]=[CH:20][N:19]=1)=[O:24])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 7268Diethyl OxalateHCID 5647602-Acetyl-4-methylpyridineHCID 2723922Sodium ethoxide

Product 1

HCID 23143392Ethyl 4-(4-methyl-2-pyridyl)-2,4-dioxobutanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Diethyl oxalate (4.42 mL) was added to sodium ethoxide (2.22 g) in ethanol (22 mL), and the mixture was stirred for 10 minutes. The above-obtained 1-(4-methyl-2-pyridyl)ethanone (2.20 g) in ethanol (22 mL) was added to the mixture, followed by stirring at room temperature for 20 minutes. Water was added to the reaction mixture, and the resultant mixture was washed with diethyl ether, and then 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-(4-methyl-2-pyridyl)-2,4-dioxobutanoic acid ethyl ester as an oily product (2.84 g, 74%).

Workup

  1. stirringby stirring at room temperature for 20 minutes
  2. washthe resultant mixture was washed with diethyl ether
  3. customthe aqueous layer was partitioned by use of saturated aqueous ammonium chloride and chloroform
  4. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  5. filtrationfollowed by filtration
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-dd086131303447cfb627f7c756da0cb3
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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