Selenium Dioxide → 3-Methyl-alpha-oxo-2-thiopheneacetaldehyde

HRID 2165614Notes

Reaction equation

HRID 2165614 reaction equation
[Se](=O)=[O:2].[C:4]([C:7]1[S:8][CH:9]=[CH:10][C:11]=1[CH3:12])(=[O:6])[CH3:5]>O1CCOCC1.O>[CH3:12][C:11]1[CH:10]=[CH:9][S:8][C:7]=1[C:4](=[O:6])[CH:5]=[O:2]

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 836533-Methyl-2-acetylthiophene

Product 1

HCID 230429823-Methyl-alpha-oxo-2-thiopheneacetaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A 34.9 g portion of selenium dioxide was dissolved in a mixture of 85 ml of dioxane and 10 ml of water with stirring and heating to 55°-60° C. A 40 g portion of -acetyl-3-methylthiophene was added and the mixture was refluxed for 6 hours, then cooled, diluted with dioxane, filtered and evaporated to dryness. The residue was dissolved in ether and the crystals which formed collected, giving 12.03 g of 3-methyl-α-oxo-2-thiopheneacetaldehyde.

Workup

  1. temperatureheating to 55°-60° C
  2. temperaturethe mixture was refluxed for 6 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customevaporated to dryness
  6. dissolutionThe residue was dissolved in ether
  7. customthe crystals which formed
  8. customcollected

Sources & evidence

ORD record
ord-f8cd987f31c84bf3856f97a91d34f023
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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