Ethyl bromoacetate → ethyl 3,5-diethyl-1H-pyrazole-1-acetate

HRID 2043750Notes

Reaction equation

HRID 2043750 reaction equation
[CH2:1]([C:3]1[CH2:7][C:6]([CH2:8][CH3:9])=[N:5][N:4]=1)[CH3:2].C(C1C=C(CC)NN=1)C.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>CN(C)C=O>[CH2:1]([C:3]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 43063673,5-diethyl-1H-pyrazoleHCID 588905493,5-diethyl-4H-pyrazole

Product 1

HCID 67458757ethyl 3,5-diethyl-1H-pyrazole-1-acetateYield 77.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,5-diethyl-4H-pyrazole (2.14 g, 17.2 mmol) (i.e. the product of Example 15, Step A) in N,N-dimethylformamide (10 mL) was added potassium carbonate (4.7 g) and ethyl bromoacetate (2.9 mL, 26.1 mmol). The reaction mixture was stirred at room temperature overnight. The resulting solids were filtered off and the filtrate was diluted with ethyl acetate, washed with water and dried over MgSO4. The reaction mixture was concentrated under reduced pressure to give 2.79 g of the title compound.

Workup

  1. filtrationThe resulting solids were filtered off
  2. additionthe filtrate was diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c5299b6f51fa4d7dbec6aa7a94348034
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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