Potassium bisulfate → HCID 11598744, compound

HRID 1452693Notes

Reaction equation

HRID 1452693 reaction equation
[CH3:1][O:2][C:3](=[O:45])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:11]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([O:29]CC3C=CC(OC)=CC=3)([C:25]([F:28])([F:27])[F:26])[C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=2)=[CH:6][CH:5]=1.C(#N)C.O.OS([O-])(=O)=O.[K+]>CCOC(C)=O>[CH3:1][O:2][C:3](=[O:45])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:11]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([OH:29])([C:21]([F:22])([F:23])[F:24])[C:25]([F:27])([F:28])[F:26])=[CH:16][CH:15]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 18373917Acetonitrile--water (1/1)HCID 87605642HCID 87605642, compound

Product 1

HCID 11598744HCID 11598744, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

76 mg (0.12 mmol) of rac 4-(1-phenyl-2-{4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-ethoxy)-benzoic acid methyl ester in 4 ml of a mixture of acetonitrile:water (9:1) were treated with 250 mg (0.46 mmol) of ceric ammonium nitrate at room temperature overnight. An additional 100 mg (0.18 mmol) of ceric ammonium nitrate were added and stirring was continued for 3 h. EtOAc and 1M KHSO4 were added and the phases were separated. The inorganic one was extracted with EtOAc, the combined organic phases were washed with brine and dried (Na2SO4) and evaporated. Column chromatography on ISOLUTE Flash NH2 with a gradient of EtOAc/n-heptane to EtOAc gave 30 mg (48%) of rac 4-{1-phenyl-2-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxy]-ethoxy}-benzoic acid methyl ester as a colorless oil, MS: 513 (M−H)−.

Workup

  1. customthe phases were separated
  2. extractionThe inorganic one was extracted with EtOAc
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-3599b05113f44a18876d236fa4f8ea1e
Source dataset
uspto-grants-2009_01
Patent number
US07473705B2

Reaction notes

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