Triacetoxyperiodinane → 5-Cyclohex-1-en-1-yl-7-isopropyl-2,2-dimethyl-6-[4-(trifluoromethyl)benzoyl]-2,3-dihydro-4H-chromen-4-one

HRID 1516708Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1516708
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[C:23]1([C:29]2[C:38]([CH:39]([OH:50])[C:40]3[CH:45]=[CH:44][C:43]([C:46]([F:49])([F:48])[F:47])=[CH:42][CH:41]=3)=[C:37]([CH:51]([CH3:53])[CH3:52])[CH:36]=[C:35]3[C:30]=2[C:31](=[O:56])[CH2:32][C:33]([CH3:55])([CH3:54])[O:34]3)[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=1>ClCCl>[C:23]1([C:29]2[C:38]([C:39](=[O:50])[C:40]3[CH:41]=[CH:42][C:43]([C:46]([F:48])([F:49])[F:47])=[CH:44][CH:45]=3)=[C:37]([CH:51]([CH3:52])[CH3:53])[CH:36]=[C:35]3[C:30]=2[C:31](=[O:56])[CH2:32][C:33]([CH3:54])([CH3:55])[O:34]3)[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=1

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 580029855-Cyclohex-1-en-1-yl-6-{hydroxy[4-(trifluoromethyl)phenyl]methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one

Produkt 1

HCID 690712705-Cyclohex-1-en-1-yl-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., 153 mg (360 μmol) of 1,1-dihydro-1,1,1-triacetoxy-1,2-benziodoxol-3(1H)-one are added to a solution of 85 mg (180 μmol) of 5-cyclohex-1-en-1-yl-6-{hydroxy[4-(trifluoromethyl)phenyl]-methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one (Example 35A) in 4 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: gradient cyclohexane→cyclohexane/dichloromethane/ethyl acetate 20:20:0.5).

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: gradient cyclohexane→cyclohexane/dichloromethane/ethyl acetate 20:20:0.5)

Quellen und Nachweise

ORD-Eintrag
ord-0d4d55163859428c9a89b1d7021841e2
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08227511B2

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