Water → HCID 86692422, compound

HRID 1748451Notes

Reaction equation

HRID 1748451 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]([CH2:20][OH:21])=[CH:16][CH:15]=2)[C:12]=1[CH3:13])=[O:7])[CH3:4].[CH3:22]I.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]([CH2:20][O:21][CH3:22])=[CH:18][CH:19]=2)[C:12]=1[CH3:13])=[O:7])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 86692421HCID 86692421, compound

Product 1

HCID 86692422HCID 86692422, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (129 mg) was added to a solution of 1-[4-(hydroxymethyl)phenyl]-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (700 mg) in N,N-dimethylformamide (13 ml) at room temperature and stirred at the same temperature for 0.5 hour. Methyl iodide (0.3 ml) was added therein and stirred at 80° C. for two hours. Methyl iodide (0.2 ml) was further added and stirred at the same temperature 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 in vacuo. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 1-[4-(methoxymethyl)phenyl]-5-methyl-1H-pyrazol-4-carboxylic acid ethyl ester (401 mg) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-0272fbe143bf4e94b683977193910682
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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