Methanol → 3-Cyclopentyl-2-(4-trifluoromethylsulfanylphenyl)propionic acid methyl ester

HRID 398481Notes

Reaction equation

HRID 398481 reaction equation
[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([S:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=2)[C:8]([OH:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:22]O>S(=O)(=O)(O)O>[CH3:22][O:9][C:8](=[O:10])[CH:7]([C:11]1[CH:16]=[CH:15][C:14]([S:17][C:18]([F:21])([F:19])[F:20])=[CH:13][CH:12]=1)[CH2:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 887MethanolHCID 22315105HCID 22315105, compound

Product 1

HCID 462213833-Cyclopentyl-2-(4-trifluoromethylsulfanylphenyl)propionic acid methyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
25 °C

Procedure

A solution of 3-cyclopentyl-2-(4-trifluoromethylsulfanyl-phenyl)propionic acid (1.33 g, 4.18 mmol) in methanol (10 mL) was treated slowly with 4 drops of concentrated sulfuric acid. The resulting reaction mixture was heated under reflux for 36 h. The reaction mixture was allowed to cool to 25° C. and then concentrated in vacuo to remove methanol. The residue was diluted with ethyl acetate (200 mL). The organic phase was washed with a saturated aqueous sodium bicarbonate solution (1×100 mL) and a saturated aqueous sodium chloride solution (1×100 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 97/3 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-trifluoromethylsulfanyl-phenyl)propionic acid methyl ester (1.37 g, 99%) as a light yellow oil: EI-HRMS m/e calcd for C16H19F3O2S (M+) 332.1058, found 332.1052.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 36 h
  4. concentrationconcentrated in vacuo
  5. customto remove methanol
  6. additionThe residue was diluted with ethyl acetate (200 mL)
  7. washThe organic phase was washed with a saturated aqueous sodium bicarbonate solution (1×100 mL)
  8. dry with materiala saturated aqueous sodium chloride solution (1×100 mL), dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b5ffa660849f444ea629729e543d9a2b
Source dataset
uspto-grants-2003_08
Patent number
US06610846B1

Reaction notes

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