Triacetoxyperiodinane → 5-(4-fluorophenyl)-7-isopropyl-2,2-dimethyl-6-[4-(trifluoromethyl)benzoyl]-2,3-dihydro-4H-chromen-4-one

HRID 1516696Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1516696
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[C:39]([CH:40]([OH:51])[C:41]3[CH:46]=[CH:45][C:44]([C:47]([F:50])([F:49])[F:48])=[CH:43][CH:42]=3)=[C:38]([CH:52]([CH3:54])[CH3:53])[CH:37]=[C:36]3[C:31]=2[C:32](=[O:57])[CH2:33][C:34]([CH3:56])([CH3:55])[O:35]3)=[CH:26][CH:25]=1>ClCCl>[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[C:39]([C:40](=[O:51])[C:41]3[CH:46]=[CH:45][C:44]([C:47]([F:49])([F:50])[F:48])=[CH:43][CH:42]=3)=[C:38]([CH:52]([CH3:53])[CH3:54])[CH:37]=[C:36]3[C:31]=2[C:32](=[O:57])[CH2:33][C:34]([CH3:55])([CH3:56])[O:35]3)=[CH:26][CH:25]=1

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 69070570Rac-5-(4-fluorophenyl)-6-{hydroxy[4-(trifluoromethyl)phenyl]methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4h-chromen-4-one

Produkt 1

HCID 580029755-(4-fluorophenyl)-7-isopropyl-2,2-dimethyl-6-[4-(trifluoromethyl)benzoyl]-2,3-dihydro-4H-chromen-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

At 0° C., 174 mg (410 μmol) of 1,1-dihydro-1,1,1-triacetoxy-1,2-benziodoxol-3(1H)-one are added to a solution of 100 mg (207 μmol) of rac-5-(4-fluorophenyl)-6-{hydroxy[4-(trifluoromethyl)-phenyl]methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one (Example 21A) in 4.5 ml of dichloromethane, and the mixture is stirred at this temperature for 4 h. The mixture is then diluted with dichloromethane and washed three times with 1 M aqueous sodium hydroxide solution. The organic phase is dried over magnesium sulfate and then concentrated under reduced pressure, and the residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 20:1).

Aufarbeitung

  1. washwashed three times with 1 M aqueous sodium hydroxide solution
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customthe residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 20:1)

Quellen und Nachweise

ORD-Eintrag
ord-a660f838fa204cc88c155e92b59a7288
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08227511B2

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