Trifluoroacetic acid → 2-[4-(4-Oxothian-3-ylidenemethyl)phenyl]propionic acid

HRID 1685800Notes

Reaction equation

HRID 1685800 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][S:5][CH2:4][C:3]1=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH3:23])[C:16]([O:18]C(C)(C)C)=[O:17])=[CH:11][CH:10]=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[O:1]=[C:2]1[CH2:7][CH2:6][S:5][CH2:4][C:3]1=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH3:23])[C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86639387tert-Butyl 2-[4-(4-oxothian-3-ylidenemethyl)phenyl]propionate

Product 1

HCID 672649512-[4-(4-Oxothian-3-ylidenemethyl)phenyl]propionic acidYield 87.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

tert-Butyl 2-[4-(4-oxothian-3-ylidenemethyl)phenyl]propionate (220 mg) obtained in Example 1 was dissolved in chloroform (2.0 ml), to the solution was added trifluoroacetic acid (2.0 ml), and the mixture was stirred at room temperature for 4 hours. The reaction mixture was quenched with water, and extracted with chloroform. The organic layer was washed with water and saturated brine, and then dried over sodium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/2) to give the title compound (160 mg, 87%).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/2)

Sources & evidence

ORD record
ord-1492c482b11342c8ad60ec78555f146c
Source dataset
uspto-grants-2012_04
Patent number
US08148421B2

Reaction notes

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