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

HRID 1167363Notes

Reaction equation

HRID 1167363 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 LM solution in THE) 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-33071fc89700440885a3dd14c2a9a74f
Source dataset
uspto-grants-2003_09
Patent number
US06617347B1

Reaction notes

Loading…