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Lithium Hydroxide → (S)-5-(4-Chlorophenyl)-6-(1,1,1-trifluoropropan-2-yloxy)nicotinic acid

HRID 1025964
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1025964
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([O:18][C@@H:19]([CH3:24])[C:20]([F:23])([F:22])[F:21])=[N:10][CH:11]=[C:12]([CH:17]=2)[C:13]([O:15]C)=[O:14])=[CH:4][CH:3]=1.[OH-].[Li+]>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([O:18][C@@H:19]([CH3:24])[C:20]([F:23])([F:21])[F:22])=[N:10][CH:11]=[C:12]([CH:17]=2)[C:13]([OH:15])=[O:14])=[CH:6][CH:7]=1
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Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 66678826(S)-methyl 5-(4-chlorophenyl)-6-(1,1,1-trifluoropropan-2-yloxy)nicotinate

Produkt 1

HCID 66678484(S)-5-(4-Chlorophenyl)-6-(1,1,1-trifluoropropan-2-yloxy)nicotinic acidAusbeute 100,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a solution of 0.860 g (S)-methyl 5-(4-chlorophenyl)-6-(1,1,1-trifluoropropan-2-yloxy)nicotinate in 9 mL tetrahydrofuran was added 3 mL of a 1M solution of lithium hydroxide in water and the mixture was stirred at room temperature overnight. The solvent was evaporated and the residue was acidified by addition of 1M hydrochloric acid till pH=2. Ethyl acetate was added and the phases were separated. The organic phase was dried over MgSO4 and the solvent was removed to yield 830 mg (100%) of the title compound as light yellow solid, MS 344.1 (M−H)−.

Aufarbeitung

  1. customThe solvent was evaporated
  2. additionthe residue was acidified by addition of 1M hydrochloric acid till pH=2
  3. additionEthyl acetate was added
  4. customthe phases were separated
  5. dry with materialThe organic phase was dried over MgSO4
  6. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-44a5f098249948d787ee0ab09fb7da40
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08729105B2

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