Water → methyl 1-benzyl-3-methyl-1H-pyrazole-4-carboxylate

HRID 2090889Notes

Reaction equation

HRID 2090889 reaction equation
[CH3:1][C:2]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][NH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C)C=O>[CH2:17]([N:4]1[CH:5]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:2]([CH3:1])=[N:3]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178498883HCID 178498883, compound

Product 1

HCID 66778578methyl 1-benzyl-3-methyl-1H-pyrazole-4-carboxylateYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3-methyl-1H-pyrazole-4-carboxylate (5.1 g) synthesized in Example 1(3) was dissolved in dimethylformamide (50 mL), potassium carbonate (5.3 g) and benzylbromide (4.6 mL) were added to at room temperature, and the mixture was stirred overnight. The reaction mixture was poured into water, and the mixture was extracted with diethyl ether. The extract was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio) to give the title object compound (5.9 g, 71%) as an oil.

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. concentrationThe extract was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio)

Sources & evidence

ORD record
ord-52ccec98129c45b8a40b08ed8617eb53
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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