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1-[2,6-Bisbenzyloxy-3-(5-methyl-7-nitroindan-4-yloxy)phenyl]ethanone → 1-[6-Benzyloxy-2-hydroxy-3-(5-methyl-7-nitroindan-4-yloxy)phenyl]ethanone

HRID 1766662
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Reaktionsgleichung

Reaktionsgleichung von HRID 1766662
C([O:8][C:9]1[C:14]([O:15][C:16]2[C:24]([CH3:25])=[CH:23][C:22]([N+:26]([O-:28])=[O:27])=[C:21]3[C:17]=2[CH2:18][CH2:19][CH2:20]3)=[CH:13][CH:12]=[C:11]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:10]=1[C:37](=[O:39])[CH3:38])C1C=CC=CC=1.FC(F)(F)C(O)=O.O.CSC>ClCCl>[CH2:30]([O:29][C:11]1[C:10]([C:37](=[O:39])[CH3:38])=[C:9]([OH:8])[C:14]([O:15][C:16]2[C:24]([CH3:25])=[CH:23][C:22]([N+:26]([O-:28])=[O:27])=[C:21]3[C:17]=2[CH2:18][CH2:19][CH2:20]3)=[CH:13][CH:12]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1
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Komponenten

4

Edukt 2

HCID 211105561-[2,6-Bisbenzyloxy-3-(5-methyl-7-nitroindan-4-yloxy)phenyl]ethanoneHCID 86597598Trifluoroacetic acid water dimethylsulfide

Produkt 1

HCID 211105611-[6-Benzyloxy-2-hydroxy-3-(5-methyl-7-nitroindan-4-yloxy)phenyl]ethanoneAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-[2,6-bisbenzyloxy-3-(5-methyl-7-nitroindan-4-yloxy)phenyl]ethanone (10.6 g) in dichloromethane (15 mL) was added a mixed solvent of trifluoroacetic acid/water/dimethylsulfide (7/3/1) (30 mL), and the mixture was stirred at room temperature for 12 hours. Adding water, the reaction mixture was extracted with dichloromethane. The organic layer was washed with water and a saturated aqueous solution of sodium hydrogen carbonate until the aqueous layer became weak alkaline, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was crystallized from ethyl acetate and hexane to give the title compound (8.07 g).

Aufarbeitung

  1. extractionAdding water, the reaction mixture was extracted with dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was crystallized from ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-c955212839704d09a6a6121a9717bc9a
Quelldatensatz
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07230031B2

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