Hydrochloric Acid → (4-Chloro-6-((2,6-dimethylpyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetic acid

HRID 591405Notes

Reaction equation

HRID 591405 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][C:5]1[C:9]2[C:10]([Cl:24])=[CH:11][C:12]([O:14][CH2:15][C:16]3[C:17]([CH3:23])=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=3)=[CH:13][C:8]=2[S:7][CH:6]=1.[OH-].[Na+].Cl>C1COCC1>[Cl:24][C:10]1[C:9]2[C:5]([CH2:4][C:3]([OH:25])=[O:2])=[CH:6][S:7][C:8]=2[CH:13]=[C:12]([O:14][CH2:15][C:16]2[C:17]([CH3:23])=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 118667003Methyl(4-chloro-6-((2,6-dimethylpyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate

Product 1

HCID 71677821(4-Chloro-6-((2,6-dimethylpyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetic acidYield 70.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl(4-chloro-6-((2,6-dimethylpyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate (140 mg) and THF (1 mL) was added 1N NaOH (1 mL) at room temperature. The mixture was stirred at room temperature for 12 h. 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 to give the title compound (95 mg).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residual solid was crystallized from EtOAc

Sources & evidence

ORD record
ord-a56cbcd5ac4b4882ad3dbb05100ed873
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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