Ethyl diazoacetate → Ethyl 3-(trimethylsilyl)-1H-pyrazole-5-carboxylate

HRID 1409972Notes

Reaction equation

HRID 1409972 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].[CH2:7]([O:9][C:10](=[O:14])[CH:11]=[N+:12]=[N-:13])[CH3:8]>>[CH3:1][Si:2]([CH3:4])([CH3:3])[C:5]1[CH:6]=[C:11]([C:10]([O:9][CH2:7][CH3:8])=[O:14])[NH:12][N:13]=1

Participants

3

Reactant 2

HCID 12192Ethyl diazoacetateHCID 66111Trimethylsilylacetylene

Product 1

HCID 178469409Ethyl 3-(trimethylsilyl)-1H-pyrazole-5-carboxylate

Conditions

Temperature
95 °C

Procedure

To a flame dried sealed tube equipped with a stir bar that was cooled under argon was added trimethylsilylacetylene (1.0 mL, 9.56 mmol) and ethyldiazoacetate (1.5 mL, 9.6 mmol). The tube was then sealed and heated to 95° C. over night. The next day the reaction was cooled to room temperature and the resulting mixture diluted with hexanes. It was then filtered. The precipitate was then washed with hexanes twice. It was then used without any further purification.

Workup

  1. customTo a flame dried
  2. customsealed tube
  3. customequipped with a stir bar that
  4. temperaturewas cooled under argon
  5. customThe tube was then sealed
  6. temperatureThe next day the reaction was cooled to room temperature
  7. filtrationIt was then filtered
  8. washThe precipitate was then washed with hexanes twice
  9. customIt was then used without any further purification

Sources & evidence

ORD record
ord-c6b4aa58852a46c9b36bc5431f9a70fa
Source dataset
uspto-grants-2014_12
Patent number
US08921401B2

Reaction notes

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