Water → 1-Benzyloxymethyl-1H-pyrazole

HRID 660489Notes

Reaction equation

HRID 660489 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:12]([O:19][CH2:20]Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>CN(C=O)C>[CH2:12]([O:19][CH2:20][N:1]1[CH:5]=[CH:4][CH:3]=[N:2]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 137983Benzyl chloromethyl ether

Product 1

HCID 216869571-Benzyloxymethyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of pyrazole (2.0 g, 29 mmol) in DMF (20 mL) is added potassium carbonate (12.4 g, 90 mmol) and benzyloxymethylchloride (4 mL, 32.3 mmol). The reaction is stirred for four days, then poured into water and extracted with EtOAc . The organic layer is washed with 1 N NaOH, dried over MgSO4 and concentrated. The residue is purified by column chromatography using EtOAc as eluent to afford the title compound as a light yellow oil: (M+1)+=189.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer is washed with 1 N NaOH
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-791074feb8574071a100c82038404028
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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