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Toluene → 1-Ethoxy-2,3-difluoro-4-(4-(3-propylcyclopentyl)cyclohex-1-enyl)benzene

HRID 1464848
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1464848
C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:20]([O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2(O)[CH2:34][CH2:33][CH:32]([CH:35]3[CH2:39][CH2:38][CH:37]([CH2:40][CH2:41][CH3:42])[CH2:36]3)[CH2:31][CH2:30]2)=[C:25]([F:44])[C:24]=1[F:45])[CH3:21]>O>[CH2:20]([O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH2:34][CH2:33][CH:32]([CH:35]3[CH2:39][CH2:38][CH:37]([CH2:40][CH2:41][CH3:42])[CH2:36]3)[CH2:31][CH:30]=2)=[C:25]([F:44])[C:24]=1[F:45])[CH3:21]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 679923521-(4-Ethoxy-2,3-difluorophenyl)-4-(3-propylcyclopentyl)cyclohexanol

Produkt 1

HCID 679922881-Ethoxy-2,3-difluoro-4-(4-(3-propylcyclopentyl)cyclohex-1-enyl)benzeneAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962Water
Lösungsmittel

Versuchsvorschrift

Toluene (50 ml) and p-toluenesulfonic acid monohydrate (0.15 g) were added to 1-(4-ethoxy-2,3-difluorophenyl)-4-(3-propylcyclopentyl)cyclohexanol (5.0 g) obtained in the first step, in a reaction vessel equipped with a Dean-Stark apparatus under an atmosphere of nitrogen. The mixture was refluxed for 1.5 hour, while forming water was removed with a Dean-Stark apparatus. After the mixture had been cooled to room temperature, the reaction solution was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane=1/10 by volume) to give 1-ethoxy-2,3-difluoro-4-(4-(3-propylcyclopentyl)cyclohex-1-enyl)benzene (3.9 g).

Aufarbeitung

  1. customobtained in the first step, in a reaction vessel
  2. customequipped with a Dean-Stark apparatus under an atmosphere of nitrogen
  3. temperatureThe mixture was refluxed for 1.5 hour
  4. customwas removed with a Dean-Stark apparatus
  5. washthe reaction solution was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane=1/10 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-a0f318190e394d1f9a320580866fc285
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08999197B2

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