Hydrochloric Acid → HCID 22926704, compound

HRID 1985291Notes

Reaction equation

HRID 1985291 reaction equation
[CH:1]([O:4][CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14](OS(C(F)(F)F)(=O)=O)[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])([CH3:3])[CH3:2].[Cl-].[Li+].Cl.[O:29]1CCO[CH2:31][CH2:30]1>>[C:30]([C:14]1[CH:13]=[C:12]([CH2:11][CH:5]([O:4][CH:1]([CH3:3])[CH3:2])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:17]=[CH:16][CH:15]=1)(=[O:29])[CH3:31]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 433294Lithium ChlorideHCID 57719687HCID 57719687, compound

Product 1

HCID 22926704HCID 22926704, compound

Conditions

Temperature
90 °C

Procedure

2.037 g of Ethyl 2-isopropoxy-3-(3-[(trifluoromethyl)sulfonyl]oxyphenyl)-propanoate, 2.5 g of ethyl [1-(1,1,1-tributylstannyl)vinyl]ether, 500 mg of lithium chloride and 186 mg of dichlorobis(triphenylphosphine) palladium were dissolved in 15 ml of dioxane, and the mixture was stirred at 90° C. overnight under nitrogen atmosphere. The solution was cooled in ice bath, added with 1N-hydrochloric acid, and extracted with ethylacetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off. The residue was purified by silica gel column chromatography, to give 1.041 g of the title compound in the 6:1 hexane-ethyl acetate fraction.

Workup

  1. temperatureThe solution was cooled in ice bath
  2. extractionextracted with ethylacetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a3f87d23012e4d5d90e14519bdecdc3e
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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