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Water → Rac 1-phenyl-2-{3-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-ethanol

HRID 1452691
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1452691
[F:1][C:2]([F:26])([F:25])[C:3]([C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1)([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)[C:4]([F:7])([F:6])[F:5].[C:27]1([CH:33]2[CH2:35][O:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>O1CCOCC1.CCOCC>[C:27]1([CH:33]([OH:34])[CH2:35][O:24][C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([C:3]([O:8][CH2:9][C:10]3[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=3)([C:4]([F:6])([F:5])[F:7])[C:2]([F:25])([F:26])[F:1])[CH:19]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 7276Styrene OxideHCID 10796Cesium carbonateHCID 86604220HCID 86604220, Verbindung

Produkt 1

HCID 87605889Rac 1-phenyl-2-{3-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-ethanolAusbeute 62,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283
Diethyl Ether
Lösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To 1 g (2.6 mmol) of 3-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenol (example 5) in 8 mL of dioxane were added 1.0 mL (8.8 mmol) of 2-phenyl-oxirane. The reaction was split in 2 portions. To each of those was added 4.28 g (13.1 mmol) of Cs2CO3 and each reaction mixture was treated for 30 min at 130° C. in the microwave. The mixtures were combined and water and ether were added. The aqueous phase was extracted with ether and the combined organic phases were washed with brine and dried (Na2SO4). After evaporation of the solvent the crude products were separated by column chromatography to give 810 mg (62%) of rac 1-phenyl-2-{3-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-ethanol as light yellow oil, MS: 500 (M)+, and 250 mg (19%) of rac 2-phenyl-2-{3-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-ethanol as light yellow oil, MS: 500 (M)+.

Aufarbeitung

  1. customThe reaction was split in 2 portions
  2. additioneach reaction mixture was treated for 30 min at 130° C. in the microwave
  3. extractionThe aqueous phase was extracted with ether
  4. washthe combined organic phases were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customAfter evaporation of the solvent the crude products
  7. customwere separated by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7f676de20d8b4b9e8e054c4f4976a154
Quelldatensatz
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07473705B2

Notizen zur Reaktion

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