Citric Acid → 1-Methyl-5-phenoxy-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1485027Notes

Reaction equation

HRID 1485027 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[CH2:14]([O:16][C:17]([C:19]1[CH:20]=[N:21][N:22]([CH3:25])[C:23]=1Br)=[O:18])[CH3:15].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CC(N(C)C)=O>[CH2:14]([O:16][C:17]([C:19]1[CH:20]=[N:21][N:22]([CH3:25])[C:23]=1[O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:18])[CH3:15]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 996PhenolHCID 11430Potassium CarbonateHCID 53302113Ethyl 5-Bromo-1-methyl-1H-pyrazole-4-carboxylate

Product 1

HCID 867185501-Methyl-5-phenoxy-1H-pyrazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
140 °C

Procedure

Phenol (30.29 g; 321.80 mmol) was dissolved in DMA and K2CO3 (88.95 g; 643.60 mmol) was added portion wise. It was stirred for 10 minutes, then 5-Bromo-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (50.0 g; 214.53 mmol) was dropped to the reaction mixture and heated up to 140° C. for 16 hours. A 10% citric acid solution was added and extracted with DCM. The organic layer was washed with sodium bicarbonate and brine, then dried and purified through column chromatography.

Workup

  1. extractionextracted with DCM
  2. washThe organic layer was washed with sodium bicarbonate and brine
  3. customdried
  4. custompurified through column chromatography

Sources & evidence

ORD record
ord-70b426cd3fd9498b96b03a79c9a057ce
Source dataset
uspto-grants-2016_08
Patent number
US09422290B2

Reaction notes

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