2-Ethoxy-1,8-difluoro-7-((4-propylcyclohexyl)methoxy)-9,10-di hydrophenanthrene-9,10-diol → 2-Ethoxy-1,8-difluoro-7-((4-propylcyclohexyl)methoxy)phenanthrene-9,10-dione

HRID 718491Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 718491
[CH2:1]([O:3][C:4]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[C:10]([F:29])[C:11]([O:18][CH2:19][CH:20]4[CH2:25][CH2:24][CH:23]([CH2:26][CH2:27][CH3:28])[CH2:22][CH2:21]4)=[CH:12][CH:13]=3)[CH:8]([OH:30])[CH:7]([OH:31])[C:6]=2[C:5]=1[F:32])[CH3:2]>CS(C)=O>[CH2:1]([O:3][C:4]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[C:10]([F:29])[C:11]([O:18][CH2:19][CH:20]4[CH2:21][CH2:22][CH:23]([CH2:26][CH2:27][CH3:28])[CH2:24][CH2:25]4)=[CH:12][CH:13]=3)[C:8](=[O:30])[C:7](=[O:31])[C:6]=2[C:5]=1[F:32])[CH3:2]

Komponenten

3

Edukt 1

HCID 680105012-Ethoxy-1,8-difluoro-7-((4-propylcyclohexyl)methoxy)-9,10-di hydrophenanthrene-9,10-diol

Produkt 1

HCID 680104992-Ethoxy-1,8-difluoro-7-((4-propylcyclohexyl)methoxy)phenanthrene-9,10-dioneAusbeute 89,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

IBX (9.03 g, 32.25 mmol) was added to 100 mL of DMSO, the resultant mixture was agitated at room temperature for 30 minutes, and then compound (64) (3.6 g, 8.062 mmol) was added thereto, and the resultant mixture was further agitated for 3 hours. The reaction mixture was filtered, 200 mL of water was added to a filtrate, and the resultant mixture was extracted with 100 mL of ethyl acetate three times. Combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, and then dried over magnesium sulfate, and a solvent was distilled off by an evaporator. The residue was recrystallized from toluene, and thus 2-ethoxy-1,8-difluoro-7-((4-propylcyclohexyl)methoxy)phenanthrene-9,10-dione (65) (3.2 g, yield 34.5%) was obtained.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. addition200 mL of water was added to a filtrate
  3. extractionthe resultant mixture was extracted with 100 mL of ethyl acetate three times
  4. washCombined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. distillationa solvent was distilled off by an evaporator
  7. customThe residue was recrystallized from toluene

Quellen und Nachweise

ORD-Eintrag
ord-3cc4134c30a94f808c262269332f5fe1
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193908B2

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