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

HRID 2377178Notes

Reaction equation

HRID 2377178 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][C:15]([O:17]C(C)(C)C)=[O:16])=[CH:9][C:4]=2[CH:3]=[CH:2]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.C(OCC)(=O)C>C1(C)C=CC=CC=1>[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 21990043HCID 21990043, compound

Product 1

HCID 219900803-(2-(1-Benzothiophen-5-yl)ethoxy)propionic acidYield 85.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 22.8 mL of toluene was dissolved 7.60 g of tert-butyl 3-[2-(1-benzothiophen-5-yl) ethoxy]propionate, and 94 mg of p-toluenesulfonic acid monohydrate was added thereto, after which the resulting mixture was refluxed for 6 hours. After the reaction mixture was cooled, water and ethyl acetate were added thereto and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue was crystallized from a toluene-cyclohexane mixture (1:4, 23 mL) to obtain 5.30 g of 3-[2-(1-benzothiophen-5-yl)ethoxy]propionic acid as light-red crystals.

Workup

  1. additionwas added
  2. temperatureafter which the resulting mixture was refluxed for 6 hours
  3. temperatureAfter the reaction mixture was cooled
  4. customthe organic layer was separated
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was crystallized from a toluene-cyclohexane mixture (1:4, 23 mL)

Sources & evidence

ORD record
ord-8cc4ee771b844d9aab5b861409109eae
Source dataset
uspto-grants-2008_12
Patent number
US07468443B2

Reaction notes

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