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Water → Ethyl 3-[4-(benzyloxy)phenyl]-3-oxo-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propanoate

HRID 1610544
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1610544
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[F:25][C:26]([F:39])([O:30][C:31]1[CH:32]=[C:33]([CH2:37]Br)[CH:34]=[CH:35][CH:36]=1)[CH:27]([F:29])[F:28].O>COCCOC>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:22])[CH:16]([CH2:37][C:33]2[CH:34]=[CH:35][CH:36]=[C:31]([O:30][C:26]([F:25])([F:39])[CH:27]([F:28])[F:29])[CH:32]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 4316945Ethyl 3-(4-(benzyloxy)phenyl)-3-oxopropanoateHCID 114603781-(Bromomethyl)-3-(1,1,2,2-tetrafluoroethoxy)benzene

Produkt 1

HCID 22261555Ethyl 3-[4-(benzyloxy)phenyl]-3-oxo-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 3-(1,1,2,2-tetrafluoroethoxy)toluene (27.8 g, 133 mmol) in ethyl acetate (250 ml) were added N-bromosuccinimide (26.1 g, 147 mmol) and 2,2′-azobis(isobutyronitrile) (440 mg, 2.67 mmol), and the mixture was heated under reflux for 5 hrs. After concentration of the reaction solution, crystals were filtered with hexane and the filtrate was concentrated to give 3-(1,1,2,2-tetrafluoroethoxy)-α-bromotoluene. To a solution of ethyl 3-[4-(benzyloxy)phenyl]-3-oxopropanoate (37.8 g, 127 mmol) in 1,2-dimethoxyethane (250 ml) was added sodium hydride (60% in oil, 5.07 g, 127 mmol) under ice-cooling, and the mixture was stirred at room temperature for 30 min. To the reaction solution was dropwise added a solution of 3-(1,1,2,2-tetrafluoroethoxy)-α-bromotoluene prepared earlier in 1,2-dimethoxyethane (50 ml), and the mixture was stirred overnight at room temperature. The reaction solution was poured into water (500 ml), and the mixture was extracted with ethyl acetate (500 ml×2). The extract was washed with water and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-1:1) and recrystallized from ethyl acetate-hexane to give the objective substance (43.4 g, 68%).

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred overnight at room temperature
  3. extractionthe mixture was extracted with ethyl acetate (500 ml×2)
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. customevaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1-1:1)
  8. customrecrystallized from ethyl acetate-hexane
  9. customto give the objective substance (43.4 g, 68%)

Quellen und Nachweise

ORD-Eintrag
ord-c9d1a5d5674e4b2987fb8da3960736cc
Quelldatensatz
uspto-grants-2006_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06982348B2

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