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

HRID 1516699Notes

Reaction equation

HRID 1516699 reaction equation
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:52])[C:41]3[CH:46]=[CH:45][C:44]([O:47][C:48]([F:51])([F:50])[F:49])=[CH:43][CH:42]=3)=[C:38]([CH:53]([CH3:55])[CH3:54])[CH:37]=[C:36]3[C:31]=2[C:32](=[O:58])[CH2:33][C:34]([CH3:57])([CH3:56])[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:52])[C:41]3[CH:42]=[CH:43][C:44]([O:47][C:48]([F:50])([F:51])[F:49])=[CH:45][CH:46]=3)=[C:38]([CH:53]([CH3:54])[CH3:55])[CH:37]=[C:36]3[C:31]=2[C:32](=[O:58])[CH2:33][C:34]([CH3:56])([CH3:57])[O:35]3)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58002959Rac-5-(4-fluorophenyl)-6-{hydroxy[4-(trifluoromethoxy)phenyl]methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4h-chromen-4-one

Product 1

HCID 580030325-(4-Fluorophenyl)-7-isopropyl-2,2-dimethyl-6-[4-(trifluoromethoxy)benzoyl]-2,3-dihydro-4H-chromen-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At 0° C., 185 mg (439 μmol) of 1,1-dihydro-1,1,1-triacetoxy-1,2-benziodoxol-3(1H)-one are added to a solution of 110 mg (220 μmol) of 5-(4-fluorophenyl)-6-{hydroxy[4-(trifluoromethoxy)-phenyl]methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one (Example 24A) 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: gradient cyclohexane→eyclohexane/ethyl acetate 10:1).

Workup

  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→eyclohexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-25d27fc3e2774b99b4b1f7011ed8aafe
Source dataset
uspto-grants-2012_07
Patent number
US08227511B2

Reaction notes

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