Triacetoxyperiodinane → HCID 58002955, compound

HRID 1516703Notes

Reaction equation

HRID 1516703 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[OH:23][CH:24]([C:47]1[CH:52]=[CH:51][C:50]([O:53][C:54]([F:57])([F:56])[F:55])=[CH:49][CH:48]=1)[C:25]1[C:26]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[C:27]2[C:32](=[CH:33][C:34]=1[CH:35]([CH3:37])[CH3:36])[O:31][C:30]([CH3:39])([CH3:38])[CH2:29][C:28]2=[O:40]>ClCCl>[CH:35]([C:34]1[CH:33]=[C:32]2[C:27]([C:28](=[O:40])[CH2:29][C:30]([CH3:39])([CH3:38])[O:31]2)=[C:26]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:25]=1[C:24](=[O:23])[C:47]1[CH:48]=[CH:49][C:50]([O:53][C:54]([F:55])([F:56])[F:57])=[CH:51][CH:52]=1)([CH3:37])[CH3:36]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58003049HCID 58003049, compound

Product 1

HCID 58002955HCID 58002955, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At 0° C., 166 mg (390 μmol) of 1,1-dihydro-1,1,1-triacetoxy-1,2-benziodoxol-3(1H)-one are added to a solution of 95 mg (197 μmol) of rac-6-{hydroxy[4-(trifluoromethoxy)phenyl]methyl}-7-iso-propyl-2,2-dimethyl-5-phenyl-2,3-dihydro-4H-chromen-4-one (Example 31A) in 3 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/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→cyclohexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-2bdcedcffdc142739a7b5a8a80414d33
Source dataset
uspto-grants-2012_07
Patent number
US08227511B2

Reaction notes

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