Diethyl Oxalate → HCID 54422680, compound

HRID 1822747Notes

Reaction equation

HRID 1822747 reaction equation
[CH3:1][C:2]([CH3:13])([CH3:12])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)=[O:4].[CH2:14]([Li])CCC.[C:19]([O:26]CC)(=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21]>O1CCCC1.CCCCCC.O>[CH3:1][C:2]([CH3:13])([CH3:12])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[CH2:14][C:19](=[O:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:4]

Participants

7

Reactant 3

HCID 7268Diethyl OxalateHCID 4270594-(2,2,2-Trimethylacetamido)pyridineHCID 178418339Butyllithium

Product 1

HCID 54422680HCID 54422680, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 10 g of 4-trimethylacetamido pyridine in 150 mL of dry tetrahydrofuran is cooled to −78° C. and 88 mL of 1.6M n-butyllithium in hexane is added in a dropwise fashion. The mixture is then stirred at 0° C. for 3 hours, cooled again to −78° C. and 21.3 g of diethyl oxalate dissolved in 190 mL of tetrahydrofuran is added in a dropwise fashion, the reaction mixture was then gradually allowed to come to room temperature. The reaction mixture is diluted with water and the product is extracted with ether. After drying over magnesium sulfate the solvent is removed in vacuo. The residue is chromatagraphed on silica gel with hexane/ether 2:1 as the eluent to afford ethyl 4-trimethylacetamido-3-pyridylpyruvate as an orange oil.

Workup

  1. temperaturecooled again to −78° C.
  2. additionis added in a dropwise fashion
  3. customto come to room temperature
  4. extractionthe product is extracted with ether
  5. dry with materialAfter drying over magnesium sulfate the solvent
  6. customis removed in vacuo

Sources & evidence

ORD record
ord-274bdd478d8c446e865140b30425732d
Source dataset
uspto-grants-2006_05
Patent number
US07037922B1

Reaction notes

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