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Water → 3-(2,4-Dichloro-phenyl)-1,1,1-trifluoro-2-[2-(2-hydroxy-ethoxy)-pyridin-4-yl]-butan-2-ol

HRID 333819
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 333819
C[O:2][C:3](=O)[CH2:4][O:5][C:6]1[CH:11]=[C:10]([C:12]([OH:27])([C:23]([F:26])([F:25])[F:24])[CH:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[CH3:14])[CH:9]=[CH:8][N:7]=1.[Li+].[BH4-].O>C1COCC1.Cl>[Cl:22][C:16]1[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=1[CH:13]([CH3:14])[C:12]([C:10]1[CH:9]=[CH:8][N:7]=[C:6]([O:5][CH2:4][CH2:3][OH:2])[CH:11]=1)([OH:27])[C:23]([F:26])([F:25])[F:24]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 962WaterHCID 4148881Lithium borohydride2×HCID 25254606{4-[2-(2,4-Dichloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-pyridin-2-yloxy}-acetic acid methyl ester

Produkt 1

HCID 574212583-(2,4-Dichloro-phenyl)-1,1,1-trifluoro-2-[2-(2-hydroxy-ethoxy)-pyridin-4-yl]-butan-2-olAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313
Hydrochloric Acid
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

{4-[2-(2,4-Dichloro-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-pyridin-2-yloxy}-acetic acid methyl ester (Example 120, 70 mg) was dissolved in THF (5 mL) and treated with LiBH4 (10 mg). After 2 h stirring at 45° C. another portion of LiBH4 (5 mg) was added and the reaction mixture further stirred at 45° C. for 2 h. After cooling down to r.t., 3 drops of 1N aqueous HCl were added, followed by water (5 mL). The reaction mixture was then extracted twice with ethyl acetate. The combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (10 g silica gel, ethyl acetate/heptane 30:70) to give the title compound as colorless foam (52 mg). MS (m/e)=410.3 (MH+).

Aufarbeitung

  1. additionwas added
  2. temperatureAfter cooling down to r.t.
  3. extractionThe reaction mixture was then extracted twice with ethyl acetate
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (10 g silica gel, ethyl acetate/heptane 30:70)

Quellen und Nachweise

ORD-Eintrag
ord-a8bf3e9e7d084056b3bdaf9cf296abdc
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08883786B2

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