Selenium Dioxide → HCID 19763563, compound

HRID 248472Notes

Reaction equation

HRID 248472 reaction equation
[C:1]([C:4]1[S:5][C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[C:8]=1[CH3:9])(=[O:3])[CH3:2].[Se](=O)=[O:15]>O1CCOCC1.O>[CH3:9][C:8]1[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[S:5][C:4]=1[C:1](=[O:3])[CH:2]=[O:15]

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 51960318781-31-2

Product 1

HCID 19763563HCID 19763563, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A 52.9 g portion of 2-acetyl-3-methylbenzothiophene was added to a solution of 36.9 g of selenium dioxide in 95 ml of dioxane and 13 ml of water at 55°-60° C. The mixture was refluxed overnight, filtered, washed with dioxane and evaporated. The residue was purified by flash column chromatography, eluting with hexane:ethyl acetate (8:2), giving 5.1 g of 3-methyl-a-oxobenzo[b]thiophene-2-acetaldehyde.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. filtrationfiltered
  3. washwashed with dioxane
  4. customevaporated
  5. customThe residue was purified by flash column chromatography
  6. washeluting with hexane:ethyl acetate (8:2)

Sources & evidence

ORD record
ord-aaef998ca4e94b508b6e079754a11a21
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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