Imidazole → 4-{[tert-Butyl(dimethyl)silyl]oxy}-1H-pyrazole

HRID 1003798Notes

Reaction equation

HRID 1003798 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.N1C=CN=C1.[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>CN(C=O)C>[Si:12]([O:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1192181H-Pyrazol-4-ol

Product 1

HCID 206558384-{[tert-Butyl(dimethyl)silyl]oxy}-1H-pyrazoleYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Hydroxypyrazole (1.16 g, 13.8 mmol) and imidazole (1.13 g, 16.6 mmol) were suspended in DMF (50 ml) under nitrogen and t-butyldimethylsilylchloride (2.3 g, 15.2 mmol) was added. After stirring 17 hours, the solvent was removed in vacuo and the residue treated with water containing 4.5 g of potassium carbonate. The mixture was extracted with two portions of chloroform and the organic layer dried over sodium sulfate. The solvent was removed in vacuo to yield product (2.58 g, 94%). NMR

Workup

  1. customthe solvent was removed in vacuo
  2. additionthe residue treated with water containing 4.5 g of potassium carbonate
  3. extractionThe mixture was extracted with two portions of chloroform
  4. dry with materialthe organic layer dried over sodium sulfate
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-2ae8c3751f4b427cbed14871ef047000
Source dataset
uspto-grants-2000_04
Patent number
US06046227

Reaction notes

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