Hydrochloric Acid → Ethyl 2-(3-cyclopropyl-1H-pyrazol-1-yl)acetate

HRID 82170Notes

Reaction equation

HRID 82170 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH:7]1([C:10]2[CH:14]=[CH:13][NH:12][N:11]=2)[CH2:9][CH2:8]1.Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].Cl>CN(C=O)C>[CH:7]1([C:10]2[CH:14]=[CH:13][N:12]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:11]=2)[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 178419915HCID 178419915, compound

Product 1

HCID 25247560Ethyl 2-(3-cyclopropyl-1H-pyrazol-1-yl)acetateYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (7.67 g, 55.56 mmol) was added to 3-cyclopropyl-1H-pyrazole (2.0 g, 18.52 mmol) in dry DMF (20 mL) at 25° C. and the mixture was stirred for 20 minutes. Ethyl bromoacetate (2.06 mL, 18.52 mmol) was added then the mixture was stirred for 2 days at room temperature. The reaction mixture was neutralized with aqueous HCl (1.0 M), extracted with ether (40 mL) and the organic extract was washed with brine (30 mL), dried over sodium sulfate then evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:EtOAc 88:12) to afford the title compound as a yellow oil in 42% yield, 1.50 g.

Workup

  1. stirringthe mixture was stirred for 2 days at room temperature
  2. extractionextracted with ether (40 mL)
  3. extractionthe organic extract
  4. washwas washed with brine (30 mL)
  5. dry with materialdried over sodium sulfate
  6. customthen evaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (hexane:EtOAc 88:12)

Sources & evidence

ORD record
ord-309d0413a21448dab29aa78f26b7caab
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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