Potassium Carbonate → [1-(4-Hydroxymethyl-benzyl)-3,5-dimethyl-1H-pyrazol-4-yl]-acetic acid methyl ester

HRID 1631926Notes

Reaction equation

HRID 1631926 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[C:6]([CH3:11])=[N:7][NH:8][C:9]=1[CH3:10].Cl[CH2:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][OH:20])=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[C:9]([CH3:10])=[N:8][N:7]([CH2:14][C:15]2[CH:22]=[CH:21][C:18]([CH2:19][OH:20])=[CH:17][CH:16]=2)[C:6]=1[CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5107660[4-(Chloromethyl)phenyl]methanolHCID 7131483methyl 2-(3,5-dimethyl-1H-pyrazol-4-yl)acetate

Product 1

HCID 66707588[1-(4-Hydroxymethyl-benzyl)-3,5-dimethyl-1H-pyrazol-4-yl]-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(3,5-dimethyl-1H-pyrazol-4-yl)-acetic acid methyl ester (3 g, 18 mmol), 4-(chloromethyl)benzyl alcohol (3.59 g, 18 mmol) and K2CO3 (5.18 g, 37 mmol) were refluxed in 10 ml acetonitrile for 3 h. After cooling, the mixture was filtered, and the solvent was removed under reduced pressure. The residue was purified by MPLC (silica gel, CH2Cl2/methanol 9:1).

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by MPLC (silica gel, CH2Cl2/methanol 9:1)

Sources & evidence

ORD record
ord-200498e28d9b432aa5e0605798e83dee
Source dataset
uspto-grants-2014_07
Patent number
US08791272B2

Reaction notes

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