Water → 2-[4-(2-Oxothiolan-3-ylidenemethyl)phenyl]propionic acid

HRID 1685816Notes

Reaction equation

HRID 1685816 reaction equation
[O:1]=[C:2]1[C:6](=[CH:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:20])[C:15]([O:17]CC)=[O:16])=[CH:10][CH:9]=2)[CH2:5][CH2:4][S:3]1.S(=O)(=O)(O)O.O>O1CCOCC1>[O:1]=[C:2]1[C:6](=[CH:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:20])[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)[CH2:5][CH2:4][S:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 67265778Ethyl 2-[4-(2-oxothiolan-3-ylidenemethyl)phenyl]propionate

Product 1

HCID 672651582-[4-(2-Oxothiolan-3-ylidenemethyl)phenyl]propionic acidYield 58%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 2-[4-(2-oxothiolan-3-ylidenemethyl)phenyl]propionate (124 mg) obtained in Example 34 was dissolved in 1,4-dioxane (4.0 ml), and then to the solution was added 30% aqueous sulfuric acid (4.0 ml). The reaction mixture was stirred at room temperature for 4 days, then added to water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=10/1) to give the title compound (65 mg, 58%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-59b3ec64bbed42768f20b6c96420d10d
Source dataset
uspto-grants-2012_04
Patent number
US08148421B2

Reaction notes

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