Sodium Hydroxide → HCID 15383979, compound

HRID 2393629Notes

Reaction equation

HRID 2393629 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([C:10]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[C:11]([CH2:17]CO)[C:12]([O:14][CH2:15]C)=[O:13])[CH:7]=[CH:8][CH:9]=1>O.C(O)C.C1(C)C=CC=CC=1>[F:3][C:4]1[CH:5]=[C:6](/[C:10](=[C:11]2\[C:12](=[O:13])[O:14][CH2:15][CH2:17]\2)/[C:20]2[CH:21]=[CH:22][C:23]([S:26]([CH3:29])(=[O:27])=[O:28])=[CH:24][CH:25]=2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 54386099HCID 54386099, compound

Product 1

HCID 15383979HCID 15383979, compoundYield 15.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

3.3 g of sodium hydroxide dissolved in 10 ml of water are added to a solution of 29.3 g of ethyl 3-(3-fluorophenyl)-3-(4-methanesulfonylphenyl)-2-(2-hydroxyethyl)-2-propenoate, prepared in Example 12, in 50 ml of ethanol and the mixture is refluxed for 2 hours. After evaporation to dryness, the residue is taken up with water, acidified with 1N hydrochloric acid and then extracted with dichloromethane. The organic phase is dried over magnesium sulfate and evaporated under vacuum to give an oily residue. The oil is solubilized in 150 ml of toluene, and 10 mg of paratoluenesulfonic acid are added. The mixture is refluxed and the water formed is removed with a Dean-Stark apparatus. After cooling, the mixture is washed with water, the organic phase is dried over magnesium sulfate and evaporated under vacuum and the residue is chromatographed on silica in t-butyl methyl ether to give 4 g of (Z)-3-[1-(3-fluorophenyl)-1-(4-methanesulfonylphenyl)methylidene]dihydrofuran-2-one (2nd product eluted) in the form of crystals melting at 153°-154° C.

Workup

  1. temperaturethe mixture is refluxed for 2 hours
  2. customAfter evaporation to dryness
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. customevaporated under vacuum
  6. customto give an oily residue
  7. temperatureThe mixture is refluxed
  8. customis removed with a Dean-Stark apparatus
  9. temperatureAfter cooling
  10. washthe mixture is washed with water
  11. dry with materialthe organic phase is dried over magnesium sulfate
  12. customevaporated under vacuum
  13. customthe residue is chromatographed on silica in t-butyl methyl ether

Sources & evidence

ORD record
ord-c979be197d274fd88c6284d658babb11
Source dataset
uspto-grants-1998_09
Patent number
US05807873

Reaction notes

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