Potassium Carbonate → 2-(4-((4-Ethoxy-2,3-difluorophenoxy)methyl)cyclohexyl)-6-propyldecahydronaphthalene

HRID 1257946Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1257946
C1(C)C=CC(S(OC[CH:12]2[CH2:17][CH2:16][CH:15]([CH:18]3[CH2:27][CH2:26][CH:25]4[CH:20]([CH2:21][CH2:22][CH:23]([CH2:28][CH2:29][CH3:30])[CH2:24]4)[CH2:19]3)[CH2:14][CH2:13]2)(=O)=O)=CC=1.[CH2:32]([O:34][C:35]1[CH:40]=[CH:39][C:38](O)=[C:37]([F:42])[C:36]=1[F:43])[CH3:33].[C:44](=[O:47])([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:32]([O:34][C:35]1[CH:40]=[CH:39][C:38]([O:47][CH2:44][CH:12]2[CH2:13][CH2:14][CH:15]([CH:18]3[CH2:27][CH2:26][CH:25]4[CH:20]([CH2:21][CH2:22][CH:23]([CH2:28][CH2:29][CH3:30])[CH2:24]4)[CH2:19]3)[CH2:16][CH2:17]2)=[C:37]([F:42])[C:36]=1[F:43])[CH3:33]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 144957634-Ethoxy-2,3-difluorophenolHCID 86666424(4-(6-Propyldecahydronaphthalene-2-yl)cyclohexyl)methyl p-toluenesulfonate

Produkt 1

HCID 679549582-(4-((4-Ethoxy-2,3-difluorophenoxy)methyl)cyclohexyl)-6-propyldecahydronaphthaleneAusbeute 59,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

(4-(6-Propyldecahydronaphthalene-2-yl)cyclohexyl)methyl p-toluenesulfonate (3.5 g) prepared in the tenth step was dissolved in DMF (50 ml). 4-Ethoxy-2,3-difluorophenol (1.6 g) and potassium carbonate (2.2 g) were added, and the mixture was stirred at 70° C. for 5 hours. The reaction mixture was washed with water, and dried over anhydrous magnesium sulfate. The DMF was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-heptane=1/20 by volume) and then by recrystallization (solvent: Solmix/n-heptane=1/4 by volume) to give 2-(4-((4-ethoxy-2,3-difluorophenoxy)methyl)cyclohexyl)-6-propyldecahydronaphthalene (2.1 g).

Aufarbeitung

  1. washThe reaction mixture was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationThe DMF was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-heptane=1/20 by volume)
  5. customby recrystallization (solvent: Solmix/n-heptane=1/4 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-7497f8b097ad431cbfd3e80f7e1522fe
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08465674B2

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