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

HRID 1516708Notes

Reaction equation

HRID 1516708 reaction equation
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

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58002985HCID 58002985, compound

Product 1

HCID 690712705-Cyclohex-1-en-1-yl-7-isopropyl-2,2-dimethyl-6-[4-(trifluoromethyl)benzoyl]-2,3-dihydro-4H-chromen-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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).

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/dichloromethane/ethyl acetate 20:20:0.5)

Sources & evidence

ORD record
ord-0d4d55163859428c9a89b1d7021841e2
Source dataset
uspto-grants-2012_07
Patent number
US08227511B2

Reaction notes

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