Triacetoxyperiodinane → 6-(4-tert-butylbenzoyl)-5-(4-fluorophenyl)-7-isopropyl-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one

HRID 1516702Notes

Reaction equation

HRID 1516702 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[C:23]([C:27]1[CH:32]=[CH:31][C:30]([CH:33]([OH:57])[C:34]2[C:35]([C:50]3[CH:55]=[CH:54][C:53]([F:56])=[CH:52][CH:51]=3)=[C:36]3[C:41](=[CH:42][C:43]=2[CH:44]([CH3:46])[CH3:45])[O:40][C:39]([CH3:48])([CH3:47])[CH2:38][C:37]3=[O:49])=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24].C(C1C=CC(C(O)C2C(C3C=CC(F)=CC=3)=C3C(=CC=2CCC)OC(C)(C)CC3=O)=CC=1)(C)(C)C>ClCCl>[C:23]([C:27]1[CH:28]=[CH:29][C:30]([C:33]([C:34]2[C:35]([C:50]3[CH:51]=[CH:52][C:53]([F:56])=[CH:54][CH:55]=3)=[C:36]3[C:41](=[CH:42][C:43]=2[CH:44]([CH3:46])[CH3:45])[O:40][C:39]([CH3:47])([CH3:48])[CH2:38][C:37]3=[O:49])=[O:57])=[CH:31][CH:32]=1)([CH3:25])([CH3:26])[CH3:24]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 58002954Rac-6-[(4-tert-butylphenyl)(hydroxy)methyl]-5-(4-fluorophenyl)-7-isopropyl-2,2-dimethyl-2,3-dihydro-4h-chromen-4-oneHCID 69070315Rac-6-[(4-tert-butylphenyl)(hydroxy)methyl]-5-(4-fluorophenyl)-7-n-propyl-2,2-dimethyl-2,3-dihydro-4h-chromen-4-one

Product 1

HCID 580030386-(4-tert-butylbenzoyl)-5-(4-fluorophenyl)-7-isopropyl-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At 0° C., 340 mg (800 μmol) of 1,1-dihydro-1,1,1-triacetoxy-1,2-benziodoxol-3(1H)-one are added to a solution of 190 mg (400 μmol) of a 2:1 mixture of rac-6-[(4-tert-butylphenyl)(hydroxy)-methyl]-5-(4-fluorophenyl)-7-isopropyl-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one (Example 27A) and rac-6-[(4-tert-butylphenyl)(hydroxy)methyl]-5-(4-fluorophenyl)-7-n-propyl-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one in 7.5 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 preparative HPLC (method 1) and subsequent 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 preparative HPLC (method 1) and subsequent column chromatography on silica gel (mobile phase: gradient cyclohexane→cyclohexane/dichloromethane/ethyl acetate 20:20:0.5)

Sources & evidence

ORD record
ord-326b956726f54ad9946c6f7e9eb0991f
Source dataset
uspto-grants-2012_07
Patent number
US08227511B2

Reaction notes

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