Acetic Acid → 3-(2-(1-Benzothiophen-5-yl)ethoxy)propionic acid

HRID 2377180Notes

Reaction equation

HRID 2377180 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:13]CC#N)=[CH:9][C:4]=2[CH:3]=[CH:2]1.O.S(=O)(=O)(O)O.C(OCC)(=O)C.[C:29]([OH:32])(=[O:31])[CH3:30]>>[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:13][CH2:30][C:29]([OH:32])=[O:31])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 962Water2×HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 21990147HCID 21990147, compound

Product 1

HCID 219900803-(2-(1-Benzothiophen-5-yl)ethoxy)propionic acid

Procedure

In 0.6 mL of acetic acid was dissolved 200 mg of 3-[2-(1-benzothiophen-5-yl)ethoxy]propiononitrile, followed by adding thereto 0.4 mL of water and 0.184 mL of sulfuric acid, and the resulting mixture was stirred at 90 to 100° C. for 1 hour. After the reaction mixture was cooled, water and ethyl acetate were added thereto and the organic layer was separated. The organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by a column chromatography (eluent; toluene ethyl acetate=3:1) to obtain 140 mg of 3-[2-(1-benzothiophen-5-yl)ethoxy]propionic acid as colorless crystals.

Workup

  1. additionby adding
  2. temperatureAfter the reaction mixture was cooled
  3. customthe organic layer was separated
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by a column chromatography (eluent; toluene ethyl acetate=3:1)

Sources & evidence

ORD record
ord-2d56498e45774d70b2b53b0764181cbe
Source dataset
uspto-grants-2008_12
Patent number
US07468443B2

Reaction notes

Loading…