Tetrabutylammonium Fluoride → 1-benzyl-1H-pyrazol-4-ol

HRID 1977456Notes

Reaction equation

HRID 1977456 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([O:13][Si](C(C)(C)C)(C)C)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([N:8]1[CH:12]=[C:11]([OH:13])[CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22996265HCID 22996265, compound

Product 1

HCID 6422181-benzyl-1H-pyrazol-4-olYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Benzyl-4-t-butyldimethylsilyloxypyrazole (3.0 g, 10.4 mmol) was dissolved in THF (20 ml) and tetrabutylammonium fluoride (52 ml of 1M solution in THF) was added. The reaction was stirred overnight and the solvent removed in vacuo. The residue was dissolved in water and extracted into diethylether. The organics dried over sodium sulfate, and the ether removed in vacuo. The residue purified by column chromatography (silica gel, chloroform→2% methanol/chloroform) to yield product (0.63 g, 35%). MS

Workup

  1. customthe solvent removed in vacuo
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted into diethylether
  4. dry with materialThe organics dried over sodium sulfate
  5. customthe ether removed in vacuo
  6. customThe residue purified by column chromatography (silica gel, chloroform→2% methanol/chloroform)

Sources & evidence

ORD record
ord-f75c0a85ddeb4ebfa76314da3933a141
Source dataset
uspto-grants-2001_05
Patent number
US06232337B1

Reaction notes

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