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2-Ethoxy-1,8-difluoro-7-propyl-9,10-dihydrophenanthrene-9,10-diol → 2-Ethoxy-1,8-difluoro-7-propylphenanthrene-9,10-dione

HRID 718487
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 718487
[CH2:1]([O:3][C:4]1[CH:17]=[CH:16][C:15]2[C:14]3[C:9](=[C:10]([F:21])[C:11]([CH2:18][CH2:19][CH3:20])=[CH:12][CH:13]=3)[CH:8]([OH:22])[CH:7]([OH:23])[C:6]=2[C:5]=1[F:24])[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:21])[C:11]([CH2:18][CH2:19][CH3:20])=[CH:12][CH:13]=3)[C:8](=[O:22])[C:7](=[O:23])[C:6]=2[C:5]=1[F:24])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

3

Edukt 1

HCID 680105352-Ethoxy-1,8-difluoro-7-propyl-9,10-dihydrophenanthrene-9,10-diol

Produkt 1

HCID 680105362-Ethoxy-1,8-difluoro-7-propylphenanthrene-9,10-dioneAusbeute 34,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

IBX (31.5 g, 112.5 mmol) was added to 100 mL of DMSO, and the resultant mixture was agitated at room temperature for 30 minutes, and then compound (57) (9.4 g, 28.11 mmol) was added 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-propylphenanthrene-9,10-dione (58) (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-d02e807913684fac8b1e94823914169b
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09193908B2

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