Potassium bisulfate → HCID 86604218, compound

HRID 1452686Notes

Reaction equation

HRID 1452686 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)([C:18]([F:21])([F:20])[F:19])[C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].OS([O-])(=O)=O.[K+]>C1COCC1>[F:15][C:14]([F:16])([F:17])[C:13]([C:10]1[CH:11]=[CH:12][C:7]([OH:6])=[CH:8][CH:9]=1)([O:22][CH2:23][C:24]1[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=1)[C:18]([F:19])([F:21])[F:20]

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 2724141Tetrabutylammonium FluorideHCID 86604216HCID 86604216, compound

Product 1

HCID 86604218HCID 86604218, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

8.39 g (17.0 mmol) of tert-butyl-dimethyl-{4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-silane was dissolved in 70 mL of THF and 25.4 ml (25.4 mmol) of 1M TBAF solution in THF was added at 0° C. The mixture was stirred at room temperature overnight, a 1M KHSO4 solution was added and the product was extracted with ethyl acetate (2×). The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated. Column chromatography on silica gel with n-heptane/ethyl acetate 5:1 as eluent yielded 4-[2,2,2-trifluoro- 1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenol as a yellow liquid, MS: 379 (M−H)−.

Workup

  1. extractionthe product was extracted with ethyl acetate (2×)
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-c81d13b8e936484bad647c303a716fa2
Source dataset
uspto-grants-2009_01
Patent number
US07473705B2

Reaction notes

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