Sodium Hydroxide → (4-Chloro-6-((1,3-dimethyl-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetic acid

HRID 591425Notes

Reaction equation

HRID 591425 reaction equation
C[O:2][C:3](=[O:24])[CH2:4][C:5]1[C:9]2[C:10]([Cl: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+]>CCO>[Cl:23][C:10]1[C:9]2[C:5]([CH2:4][C:3]([OH:24])=[O:2])=[CH:6][S:7][C:8]=2[CH:13]=[C:12]([O:14][CH2:15][C:16]2[N:20]([CH3:21])[N:19]=[C:18]([CH3:22])[CH:17]=2)[CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118667006Methyl(4-chloro-6-((1,3-dimethyl-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetate

Product 1

HCID 89768924(4-Chloro-6-((1,3-dimethyl-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetic acidYield 90.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of methyl(4-chloro-6-((1,3-dimethyl-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetate (162 mg) and EtOH (3 mL) was added 1N NaOH (1 mL) at room temperature, and the mixture was refluxed for 1 h. The mixture was concentrated in vacuo, neutralized with 1N HCl at 0° C. and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was crystallized from EtOAc-hexane to give the title compound (141 mg).

Workup

  1. temperaturethe mixture was refluxed for 1 h
  2. concentrationThe mixture was concentrated in vacuo
  3. customneutralized with 1N HCl at 0° C.
  4. extractionextracted with EtOAc
  5. customThe organic layer was separated
  6. washwashed successively with water and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was crystallized from EtOAc-hexane

Sources & evidence

ORD record
ord-b04ac44259e34bcbacaddef528cf12a2
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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