Diethyl Oxalate → HCID 15870414, compound

HRID 1741254Notes

Reaction equation

HRID 1741254 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-293e85f8c8d64c548a51c90d4477fd4d
Source dataset
uspto-grants-1999_10
Patent number
US05973152

Reaction notes

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