Tetrahydrofuran → (6-((1-Methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetic acid

HRID 591409Notes

Reaction equation

HRID 591409 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][CH2:16][C:17]3[N:21]([CH3:22])[N:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)=[CH:14][C:9]=2[S:8][CH:7]=1)C.C1COCC1.[OH-].[Na+]>CCO>[CH3:22][N:21]1[C:17]([CH2:16][O:15][C:13]2[CH:12]=[CH:11][C:10]3[C:6]([CH2:5][C:4]([OH:27])=[O:3])=[CH:7][S:8][C:9]=3[CH:14]=2)=[CH:18][C:19]([C:23]([F:25])([F:26])[F:24])=[N:20]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 89768891Ethyl(6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetate

Product 1

HCID 89768822(6-((1-Methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetic acidYield 87.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of ethyl(6-((1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methoxy)-1-benzothiophen-3-yl)acetate (129.8 mg), THF (2.0 mL) and EtOH (2.0 mL) was added 1N NaOH (0.98 mL) at room temperature. The mixture was stirred at room temperature for 3 h under nitrogen atmosphere. The mixture was concentrated. The residue was neutralized with 1N HCl and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The solid was crystallized from EtOAc-hexane to give the title compound (106 mg).

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe solid was crystallized from EtOAc-hexane

Sources & evidence

ORD record
ord-1b47c7aff9874c79aa3f9db9e85b0414
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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