Hydrochloric Acid → (6-((1,3-Dimethyl-1H-pyrazol-5-yl)methoxy)-4-methyl-1-benzothiophen-3-yl)acetic acid

HRID 591397Notes

Reaction equation

HRID 591397 reaction equation
C[O:2][C:3](=[O:24])[CH2:4][C:5]1[C:9]2[C:10]([CH3:23])=[CH:11][C:12]([O:14][CH2:15][C:16]3[N:20]([CH3:21])[N:19]=[C:18]([CH3:22])[CH:17]=3)=[CH:13][C:8]=2[S:7][CH:6]=1.[OH-].[Na+].Cl>CCO>[CH3:21][N:20]1[C:16]([CH2:15][O:14][C:12]2[CH:11]=[C:10]([CH3:23])[C:9]3[C:5]([CH2:4][C:3]([OH:24])=[O:2])=[CH:6][S:7][C:8]=3[CH:13]=2)=[CH:17][C:18]([CH3:22])=[N:19]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 118667002Methyl(6-((1,3-dimethyl-1H-pyrazol-5-yl)methoxy)-4-methyl-1-benzothiophen-3-yl)acetate

Product 1

HCID 89768917(6-((1,3-Dimethyl-1H-pyrazol-5-yl)methoxy)-4-methyl-1-benzothiophen-3-yl)acetic acidYield 79.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of methyl(6-((1,3-dimethyl-1H-pyrazol-5-yl)methoxy)-4-methyl-1-benzothiophen-3-yl)acetate (143 mg) and EtOH (2 mL) was added 1N NaOH (0.42 mL) at room temperature, and the mixture was refluxed for 30 min. The mixture was neutralized with 1N HCl at room temperature and extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residual solid was crystallized from EtOAc-hexane to give the title compound (109 mg).

Workup

  1. temperaturethe mixture was refluxed for 30 min
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residual solid was crystallized from EtOAc-hexane

Sources & evidence

ORD record
ord-9344cfa701e44ca588adc7afe2c440fe
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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