Sodium Hydroxide → 2-(2-(1-Benzothiophene-5-yl)ethoxy)acetic acid

HRID 1007926Notes

Reaction equation

HRID 1007926 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][O:12][CH2:13][C:14](N3CCCCC3)=[O:15])[CH:8]=[CH:9][C:2]1=2.[OH-:22].[Na+]>C(O)C.O>[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][O:12][CH2:13][C:14]([OH:15])=[O:22])[CH:8]=[CH:9][C:2]1=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 226663742-(2-Benzo[b]thiophen-5-ylethoxy)-1-piperidino-1-ethanone

Product 1

HCID 219900582-(2-(1-Benzothiophene-5-yl)ethoxy)acetic acidYield 74.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In a mixture of 58 mL of ethanol and 6 mL of water is dissolved 6.40 g of 2-(2-benzo[b]thiophen-5-ylethoxy)-1-piperidino-1-ethanone, to which is added 1.27 g of sodium hydroxide. The mixture is heated under reflux for 4 hours. After cooling the mixture, the deposited matter is collected by filtration. The deposited matter is added to a mixture of ethyl acetate and water, pH is adjusted to 1.5 with 2 mol/L hydrochloric acid, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure to obtain 3.72 g of 2-(2-benzo[b]thiophen-5-ylethoxy)-acetic acid as a colorless crystalline product.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter cooling the mixture
  4. filtrationthe deposited matter is collected by filtration
  5. additionThe deposited matter is added to a mixture of ethyl acetate and water, pH
  6. customthe organic layer is separated
  7. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-0b252585547a46fe8a2240492bf34990
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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