1-Bromodecane → Methyl 1-decylpyrazole-4-carboxylate

HRID 1977272Notes

Reaction equation

HRID 1977272 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH3:9])=[O:7])[CH:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(OCC)(=O)C>CN(C)C=O>[CH2:17]([N:1]1[CH:5]=[C:4]([C:6]([O:8][CH3:9])=[O:7])[CH:3]=[N:2]1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 81731-BromodecaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 9793760Methyl 1H-pyrazole-4-carboxylate

Product 1

HCID 21997475Methyl 1-decylpyrazole-4-carboxylateYield 91.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl pyrazole-4-carboxylate (10 g) in N,N-dimethylformamide (100 ml) was treated with potassium carbonate (10.95 g) and 1-bromodecane (19.31 g) and the mixture was stirred for 16 hours at room temperature. Ethyl acetate was added and the solution was washed with water (6x), dried over magnesium sulfate and the evaporated residue was purified by silica gel chromatography (5:1 hexane-ethyl acetate elution) to give methyl 1-decylpyrazole-4-carboxylate (19.4 g) as a white solid.

Workup

  1. washthe solution was washed with water (6x)
  2. dry with materialdried over magnesium sulfate
  3. customthe evaporated residue was purified by silica gel chromatography (5:1 hexane-ethyl acetate elution)

Sources & evidence

ORD record
ord-f0658be6345648c9a1efd316d7a6c00f
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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