Trifluoroacetic anhydride → HCID 178458882, compound

HRID 703372Notes

Reaction equation

HRID 703372 reaction equation
[C:1]([C:5]1[C:6](=[O:21])[CH2:7][CH:8]([C:12]2[CH:17]=[CH:16][C:15]([S:18](C)=O)=[CH:14][CH:13]=2)[CH2:9][C:10]=1[OH:11])(=[O:4])[CH2:2][CH3:3].FC(F)(F)C(OC(=O)C(F)(F)F)=O>>[C:1]([C:5]1[C:6](=[O:21])[CH2:7][CH:8]([C:12]2[CH:13]=[CH:14][C:15]([SH:18])=[CH:16][CH:17]=2)[CH2:9][C:10]=1[OH:11])(=[O:4])[CH2:2][CH3:3]

Participants

3

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 178458885HCID 178458885, compound

Product 1

HCID 178458882HCID 178458882, compound

Procedure

To 5 g (0.0163 mol) of 2-propionyl-3-hydroxy-5-(4-(methylsulfinyl)phenyl)cyclohex-2-en-1-one in a flask cooled in an ice-water bath was added 25 mL (0.177 mol) of trifluoroacetic anhydride dropwise over 5 minutes. The ice-water bath was removed and the solution stirred at ambient temperature for 3 hours. The solvent was removed in vacuo and the oil remaining was dissolved in 82 mL of 1N NaOH and the solution stirred at ambient temperature overnight. The mixture was diluted with 1200 mL of water, filtered and the filtrate acidified with 5 mL of concentrated HCl with the product precipitating as an oily solid. The product was dissolved in 150 mL of methylene chloride and the solution washed twice with 150 mL portions of water and dried over Na2SO4. Removal of the solvent in vacuo gave the above named product in a yield of 4.0 g (88.7 percent of theoretical).

Workup

  1. customThe ice-water bath was removed
  2. customThe solvent was removed in vacuo
  3. dissolutionthe oil remaining was dissolved in 82 mL of 1N NaOH
  4. stirringthe solution stirred at ambient temperature overnight
  5. additionThe mixture was diluted with 1200 mL of water
  6. filtrationfiltered
  7. customprecipitating as an oily solid
  8. dissolutionThe product was dissolved in 150 mL of methylene chloride
  9. washthe solution washed twice with 150 mL portions of water
  10. dry with materialdried over Na2SO4
  11. customRemoval of the solvent in vacuo
  12. customgave the

Sources & evidence

ORD record
ord-8fd9a592adf6430e9a583dba1d9a2d1d
Source dataset
uspto-grants-1991_01
Patent number
US04983211

Reaction notes

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