Dimethylformamide → 3-benzyloxy-1-phenyl-1H-pyrazol-4-ylmethyl acetate

HRID 1295252Notes

Reaction equation

HRID 1295252 reaction equation
[CH2:1]([O:8][C:9]1[C:13]([CH2:14]C(O)=O)=[CH:12][N:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[C:26](=[O:29])([O-])[O-:27].[K+].[K+].[CH3:32]N(C)C=O>O>[C:26]([O:27][CH2:14][C:13]1[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:10][N:11]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:12]=1)(=[O:29])[CH3:32]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 694305053-benzyloxy-1-phenyl-1H-pyrazol-4-ylacetic acid

Product 1

HCID 694263823-benzyloxy-1-phenyl-1H-pyrazol-4-ylmethyl acetateYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-benzyloxy-1-phenyl-1H-pyrazol-4-ylacetic acid (2.47 g), methyl iodide (0.75 ml), potassium carbonate (2.21 g) and N,N-dimethylformamide (25 ml) was stirred at room temperature for 1 hr. The reaction solution was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and 3-benzyloxy-1-phenyl-1H-pyrazol-4-ylmethyl acetate (2.55 g, yield 99%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point: 74–75° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c19111e8d65547078fc6e7f5b0ad53b8
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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