Tetrabutylammonium Fluoride → HCID 21090758, compound

HRID 351241Notes

Reaction equation

HRID 351241 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([Si](C)(C)[O:24][CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[N:38]([C:39]3[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=3)[N:37]=[C:36]([C:47]([O:50][CH3:51])([CH3:49])[CH3:48])[CH:35]=2)=[CH:30][CH:29]=1)(C)(C)C>C1COCC1>[CH3:51][O:50][C:47]([C:36]1[CH:35]=[C:34]([C:31]2[CH:32]=[CH:33][C:28]([O:27][CH2:26][CH2:25][OH:24])=[CH:29][CH:30]=2)[N:38]([C:39]2[CH:40]=[CH:41][C:42]([O:45][CH3:46])=[CH:43][CH:44]=2)[N:37]=1)([CH3:49])[CH3:48]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69331790HCID 69331790, compound

Product 1

HCID 21090758HCID 21090758, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1M solution of tetra-n-butylammonium fluoride in THF (0.24 mg) was added to a solution of 5-[4-(2-{ [tert-butyl-(dimethyl)silyl]oxy}ethoxy)phenyl]-3-(1-methoxy-1-methylethyl)-1-(4-methoxyphenyl)-1H-pyrazole (98 mg) in THF (2 ml) under ice bath cooling. The reaction mixture was stirred at same temperature for 1 hour. The mixture was partitioned between ethyl acetate and H2O. The organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by preparative thin layer silica gel chromatography developed by 50% AcOEt/n-hexane. The seaparated silica gel was extracted with 10% MeOH/CHCl3 and the solvent was evaporated in vacuo to give 2-{4-[3-(1-methoxy-1-methylethyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]phenoxy}ethanol (66 mg) as an oil.

Workup

  1. temperaturecooling
  2. customThe mixture was partitioned between ethyl acetate and H2O
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative thin layer silica gel chromatography
  7. extractionThe seaparated silica gel was extracted with 10% MeOH/CHCl3
  8. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-6593f9307a774e23b4be25ae13119625
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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