Methanol → HCID 46221382, compound

HRID 1860134Notes

Reaction equation

HRID 1860134 reaction equation
[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)[C:8]([OH:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:19]O>S(=O)(=O)(O)O>[CH3:19][O:9][C:8](=[O:10])[CH:7]([C:11]1[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[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 120694883-Cyclopentyl-2-(4-methylsulfanyl-phenyl)propionic acid

Product 1

HCID 46221382HCID 46221382, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
25 °C

Procedure

A solution of 3-cyclopentyl-2-(4-methylsulfanyl-phenyl)propionic acid (500 mg, 1.89 mmol) in methanol (8 mL) was treated slowly with 2 drops of concentrated sulfuric acid. The resulting reaction mixture was heated under reflux for 15 h. The reaction mixture was allowed to cool to 25° C. and then concentrated in vacuo. The orange residue was partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo to provide pure 3-cyclopentyl-2-(4-methylsulfanyl-phenyl)propionic acid methyl ester (481 mg, 91%) as a yellow-orange oil which was used without further purification: EI-HRMS m/e calcd for C16H22O2S (M+) 278.1341, found 278.1347.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 15 h
  4. concentrationconcentrated in vacuo
  5. customThe orange residue was partitioned between water and ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e7ad4aa3ac4a492ab389a4f6e6391250
Source dataset
uspto-grants-2003_03
Patent number
US06528543B1

Reaction notes

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