Potassium bisulfate → Rac 4-(2-phenyl-2-{4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-ethoxy)-benzaldehyde

HRID 1452702Notes

Reaction equation

HRID 1452702 reaction equation
[C:1]1([CH:7]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=3)([C:29]([F:32])([F:31])[F:30])[C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=2)[CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(#N)C.O.[OH:47]S([O-])(=O)=O.[K+]>CCOC(C)=O>[C:1]1([CH:7]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=3)([C:29]([F:30])([F:31])[F:32])[C:25]([F:28])([F:26])[F:27])=[CH:20][CH:19]=2)[CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([CH:16]=[O:47])=[CH:14][CH:15]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 18373917Acetonitrile--water (1/1)HCID 87604960HCID 87604960, compound

Product 1

HCID 87604503Rac 4-(2-phenyl-2-{4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-ethoxy)-benzaldehydeYield 48%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

90 mg (0.15 mmol) of rac 1-(1-phenyl-2-p-tolyloxy-ethoxy)-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-benzene in 3 ml of a mixture of acetonitrile:water (9:1) were treated with 100 mg (0.18 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. 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, dried (Na2SO4) and evaporated. Column chromatography on silica gel gave 44 mg (48%) of rac 4-(2-phenyl-2-{4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-ethoxy)-benzaldehyde, MS: 663 (M+OAc)−.

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-9eab85f8ab9646eaa57ac5f61c8330a0
Source dataset
uspto-grants-2009_01
Patent number
US07473705B2

Reaction notes

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