Water → 4-(Benzo(b)thienyl)acetic acid

HRID 408561Notes

Reaction equation

HRID 408561 reaction equation
C([O:5][C:6](=[O:19])[CH:7]([C:10]1[C:18]2[CH:17]=[CH:16][S:15][C:14]=2[CH:13]=[CH:12][CH:11]=1)C#N)(C)(C)C.[OH-].[K+].O>C(O)CO>[S:15]1[CH:16]=[CH:17][C:18]2[C:10]([CH2:7][C:6]([OH:19])=[O:5])=[CH:11][CH:12]=[CH:13][C:14]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 66751041HCID 66751041, compound

Product 1

HCID 758334-(Benzo(b)thienyl)acetic acid

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of benzo[b]thiophen-4-yl-cyano-acetic acid tert-butyl ester (1 eq.) in ethylene glycol were added an aqueous solution of 38 percent (w/w) potassium hydroxide and water. The reaction was heated at 95° C. for 2 h. The reaction mixture was partitioned between water and toluene, and the organic layer was discarded. The aqueous layer was acidified with aqueous HCl (6N) until pH=2 and extracted three times with EtOAc. The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure. To the resulting residue was added a mixture of Et2O/pentane and the precipitate was collected by filtration to provide benzo[b]thiophen-4-yl-acetic acid.

Workup

  1. customThe reaction mixture was partitioned between water and toluene
  2. extractionextracted three times with EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. additionTo the resulting residue was added
  7. additiona mixture of Et2O/pentane
  8. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-bbe3c593b8ee4781b64deaaec9c39821
Source dataset
uspto-grants-2014_06
Patent number
US08759334B2

Reaction notes

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