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

HRID 1003799Notes

Reaction equation

HRID 1003799 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-e30411bb63e844f69ca17556e5a1936b
Source dataset
uspto-grants-2000_04
Patent number
US06046227

Reaction notes

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