Diethyl Oxalate → HCID 15870414, compound

HRID 379687Notes

Reaction equation

HRID 379687 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 zmixture 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 farther 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-70311de3fa71442e940a26947180f5bf
Source dataset
uspto-grants-2001_10
Patent number
US06300360B1

Reaction notes

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