Imidazole → HCID 178469392, compound

HRID 1396499Notes

Reaction equation

HRID 1396499 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.[O:14]=[C:15]1[NH:19][N:18]=[C:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:16]1>C(#N)C.O>[Si:1]([O:14][C:15]1[NH:19][N:18]=[C:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:16]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 225371Ethyl 5-Oxo-4,5-dihydro-1H-pyrazole-3-carboxylate

Product 1

HCID 178469392HCID 178469392, compoundYield 44.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Tert-butyldimethylsilyl chloride (6.05 g, 40.15 mmol) and imidazole (2.92 g, 42.82 mmol) were added to a stirred solution of ethyl 5-oxo-4,5-dihydro-1H-pyrazole-3-carboxylate (4.18 g, 26.76 mmol) in ACN (90 mL). The mixture was stirred at room temperature for 30 minutes, then diluted with water and extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo to yield ethyl 5-{[tert-butyl(dimethyl)silyl]oxy}-1H-pyrazole-3-carboxylate (3.2 g, 44% yield) as a yellow solid, that was used in the next step without further purification.

Workup

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-00698d8ef3fe4010a27adf99423e6c4c
Source dataset
uspto-grants-2014_12
Patent number
US08901125B2

Reaction notes

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