Diethyl Oxalate → HCID 15870414, compound

HRID 365486Notes

Reaction equation

HRID 365486 reaction equation
[Na].[C:2]([O:9][CH2:10][CH3:11])(=[O:8])[C:3]([O:5]CC)=O.[CH3:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([CH3:20])[C:14]=1[C:21](=[O:25])[CH2:22][CH2:23][CH3:24]>CCO>[CH2:23]([CH:22]([C:21](=[O:25])[C:14]1[C:15]([CH3:20])=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=1[CH3:12])[C:3](=[O:5])[C:2]([O:9][CH2:10][CH3:11])=[O:8])[CH3:24]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 2511601-(2,4,6-trimethylphenyl)butan-1-oneHCID 5360545Sodium2×

Product 1

HCID 15870414HCID 15870414, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

Sodium (1.0 g, 42.1 mmol, spheres) was cautiously added to 25 mL of absolute EtOH with stirring. After the sodium had dissolved, diethyl oxalate (6.0 g, 42.1 mmol) was added dropwise to the resulting solution at 0° C., followed by addition of a solution of 2',4',6'-trimethylbutyrophenone (8 g, 42.1 mmol) in 5 mL of absolute EtOH. The reaction mixture was slowly warmed to 50° C. and stirred overnight. The solvent was then evaporated. The resulting residue was washed with hexane, diluted with water, acidified with 1 N HCl, and then extracted with ether. The extracts were washed with brine, dried over Na2SO4 and concentrated to give 6.5 g of an oil which was used in the next reaction without further purification.

Workup

  1. stirringstirred overnight
  2. customThe solvent was then evaporated
  3. washThe resulting residue was washed with hexane
  4. additiondiluted with water
  5. extractionextracted with ether
  6. washThe extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-69734882ed034e54a02ab73a63810091
Source dataset
uspto-grants-2000_10
Patent number
US06127399

Reaction notes

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