Water → HCID 15407394, compound

HRID 850076Notes

Reaction equation

HRID 850076 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:10]2[CH:14]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:12]=[N:11]2)[CH:6]=[CH:7][C:8]=1[OH:9])#[N:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][C@@H:28]([CH3:31])[CH2:29][CH3:30].O>CN(C)C=O.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([N:10]2[CH:14]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:12]=[N:11]2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:27][C@@H:28]([CH3:31])[CH2:29][CH3:30])#[N:2]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 54641671-Bromo-2-methylbutane, (+)-HCID 15407383Ethyl 1-(3-cyano-4-hydroxyphenyl)pyrazole-4-carboxylate

Product 1

HCID 15407394HCID 15407394, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution (10 ml) of ethyl 1-(3-cyano-4-hydroxyphenyl)pyrazole-4-carboxylate (1.5 g) in dimethylformamide were added potassium carbonate (0.91 g) and (S)-(+)-1-bromo-2-methylbutane (1 g) with stirring, and the mixture was heated at 90° C. for 2 hours. After the completion of the reaction, the reaction mixture was poured into water and the mixture was acted with ethyl acetate, washed with water and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was recrystallized from isopropyl ether to give 1.7 g of ethyl 1-(3-cyano-4-((S)-2-methylbutoxy)phenyl)pyrazole-4-carboxylate, melting point 105-106° C.

Workup

  1. customAfter the completion of the reaction
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-e59d5e7e0df94c7a8d2c7f227392c8e7
Source dataset
uspto-grants-2000_01
Patent number
US06015829

Reaction notes

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