Hydrochloric Acid → Ethyl 2-(3-isopropyl-5-methyl-1H-pyrazol-1-yl)acetate

HRID 82214Notes

Reaction equation

HRID 82214 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH:8]([C:11]1[NH:15][N:14]=[C:13]([CH3:16])[CH:12]=1)([CH3:10])[CH3:9].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C.CCOC(C)=O>[CH:8]([C:11]1[CH:12]=[C:13]([CH3:16])[N:14]([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[N:15]=1)([CH3:10])[CH3:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 178425249HCID 178425249, compound

Product 1

HCID 70847751Ethyl 2-(3-isopropyl-5-methyl-1H-pyrazol-1-yl)acetateYield 34%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl bromoacetate (1.00 mL, 9.03 mmol) was added to 5-isopropyl-3-methyl-1H-pyrazole (1.07 g, 8.60 mmol) and potassium carbonate (3.57 g, 25.9 mol) in DMF (10 mL). The mixture was stirred at room temperature for 17 hours then EtOAc (20 mL) and aqueous HCl (20 mL, 1 M) were added. The organic phase was dried over magnesium sulphate then evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:EtOAc 4:1) to afford the title compound as a yellow oil in 34% yield, 607 mg.

Workup

  1. dry with materialThe organic phase was dried over magnesium sulphate
  2. customthen evaporated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (hexane:EtOAc 4:1)

Sources & evidence

ORD record
ord-da6b1df621914c8196e14737efe19afb
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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