Hydrochloric Acid → (4-Methyl-6-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetic acid

HRID 591399

Reaktionsgleichung

Reaktionsgleichung von HRID 591399
C[O:2][C:3](=[O:28])[CH2:4][C:5]1[C:9]2[C:10]([CH3:27])=[CH:11][C:12]([O:14][CH2:15][C:16]3[C:17]([CH3:26])=[N:18][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:21]=3)=[CH:13][C:8]=2[S:7][CH:6]=1.[OH-].[Na+].Cl>CCO>[CH3:27][C:10]1[C:9]2[C:5]([CH2:4][C:3]([OH:28])=[O:2])=[CH:6][S:7][C:8]=2[CH:13]=[C:12]([O:14][CH2:15][C:16]2[C:17]([CH3:26])=[N:18][C:19]([C:22]([F:24])([F:23])[F:25])=[CH:20][CH:21]=2)[CH:11]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 89775295Methyl(4-methyl-6-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate

Produkt 1

HCID 89767990(4-Methyl-6-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetic acidAusbeute 76,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a mixture of methyl(4-methyl-6-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate (222.5 mg) and EtOH (5 mL) was added 1N NaOH (1 mL) at room temperature, and the mixture was refluxed for 2 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 residue was crystallized from EtOAc-hexane to give the title compound (165 mg).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 2 h
  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 residue was crystallized from EtOAc-hexane

Quellen und Nachweise

ORD-Eintrag
ord-0e267e3cda8d49ffb652e7b32de5d035
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238639B2

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