Water → 1-(4-ethoxyphenyl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1748455Notes

Reaction equation

HRID 1748455 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[CH:9]=[N:10][N:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[C:12]=1[CH3:13])=[O:7])[CH3:4].[CH2:21](I)[CH3:22].O>CN(C)C=O>[CH2:3]([O:5][C:6]([C:8]1[CH:9]=[N:10][N:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:21][CH3:22])=[CH:18][CH:19]=2)[C:12]=1[CH3:13])=[O:7])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 866924241-(4-hydroxyphenyl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester

Product 1

HCID 866924251-(4-ethoxyphenyl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (234 mg) was added to a solution of 1-(4-hydroxyphenyl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (1.2 g) in N,N-dimethylformamide (12 ml) at room temperature, stirred at the same temperature for 30 minutes, then ethyl iodide (0.8 ml) was added therein and the mixture was stirred at 80° C. for an hour. After completion of the reaction, the reaction solution was cooled to room temperature, water was added therein and extracted with ethyl acetate three times. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 1-(4-ethoxyphenyl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (1.32 g) as a white solid.

Workup

  1. stirringthe mixture was stirred at 80° C. for an hour
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate three times
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8053f939ec634b428aab80e320c683d6
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

Loading…