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Sodium Hydroxide → (2RS,3RS)-3-(3-chlorophenyl)-3-hydroxy-2-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]propionic acid

HRID 1610755
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1610755
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:30])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25])=[CH:18][CH:17]=2)[C:10]([O:12]CC)=[O:11])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>O1CCCC1CCO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:30])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][C:23]([F:28])([F:29])[C:24]([F:26])([F:27])[F:25])=[CH:18][CH:17]=2)[C:10]([OH:12])=[O:11])[CH:5]=[CH:6][CH:7]=1
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Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 86593311ethyl (2RS,3RS)-3-(3-chlorophenyl)-3-hydroxy-2-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]propionate

Produkt 1

HCID 22262096(2RS,3RS)-3-(3-chlorophenyl)-3-hydroxy-2-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]propionic acidAusbeute 79,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 119895722-(Oxolan-2-yl)ethan-1-olLösungsmittel

Versuchsvorschrift

To a solution of ethyl (2RS,3RS)-3-(3-chlorophenyl)-3-hydroxy-2-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]propionate (3.84 g, 8.52 mmol) in tetrahydrofuran-ethanol (20 ml—20 ml) was added 1N sodium hydroxide (17 ml, 17 mmol) at room temperature, and the mixture was stirred overnight at room temperature. After completion of the reaction, the organic solvent was evaporated under reduced pressure, and the aqueous layer was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was recrystallized from hexane-ethyl acetate to give (2RS,3RS)-3-(3-chlorophenyl)-3-hydroxy-2-[4-(2,2,3,3,3-pentafluoropropyl)benzyl]propionic acid (2.85 g, 79%) as colorless crystals.

Aufarbeitung

  1. customAfter completion of the reaction
  2. customthe organic solvent was evaporated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from hexane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-741184d4e65b443d83fdaaf8cbf7fe80
Quelldatensatz
uspto-grants-2006_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06982348B2

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