HCID 18364408, compound → HCID 17820729, compound

HRID 380241Notes

Reaction equation

HRID 380241 reaction equation
[Cl:1][C:2]1[C:3]2[CH:12]=[C:11]3[O:13][CH2:14][O:15][C:10]3=[CH:9][C:4]=2[S:5][C:6]=1[CH2:7][OH:8]>O1CCOCC1.C(OCC)(=O)C.O=[Mn]=O>[Cl:1][C:2]1[C:3]2[CH:12]=[C:11]3[O:13][CH2:14][O:15][C:10]3=[CH:9][C:4]=2[S:5][C:6]=1[CH:7]=[O:8]

Participants

5

Reactant 1

HCID 18364408HCID 18364408, compound

Product 1

HCID 17820729HCID 17820729, compound

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

3.5 equivalents of MnO2 are added at ambient temperature under an inert atmosphere to a suspension of 0.12 mol of the compound obtained in Step C in 925 ml of anhydrous dioxane. After 3.5 hours' reaction at reflux, the reaction mixture is filtered while hot over Celite and rinsed with dioxane; the filtrate is then concentrated under reduced pressure. The residue obtained is taken up in 100 ml of ethyl acetate and the solution obtained is refluxed and then returned to ambient temperature. A precipitate forms, which is filtered off, rinsed with ethyl acetate and then with water and pentane, and finally dried in vacuo, allowing the expecting product to be isolated.

Workup

  1. customAfter 3.5 hours' reaction
  2. temperatureat reflux
  3. filtrationthe reaction mixture is filtered while hot over Celite
  4. washrinsed with dioxane
  5. concentrationthe filtrate is then concentrated under reduced pressure
  6. customThe residue obtained
  7. customthe solution obtained
  8. temperatureis refluxed
  9. customreturned to ambient temperature
  10. filtrationA precipitate forms, which is filtered off
  11. washrinsed with ethyl acetate
  12. dry with materialwith water and pentane, and finally dried in vacuo
  13. customto be isolated

Sources & evidence

ORD record
ord-8896757702694271ad44b325e5947096
Source dataset
uspto-grants-2001_10
Patent number
US06302837B1

Reaction notes

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