Pyrazole → 1-Benzyloxymethyl-1H-pyrazole

HRID 660733Notes

Reaction equation

HRID 660733 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[Li]CCCC.[CH2:11](Cl)[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[CH2:13]([O:12][CH2:11][N:1]1[CH:5]=[CH:4][CH:3]=[N:2]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 137983Benzyl chloromethyl etherHCID 178418339Butyllithium

Product 1

HCID 216869571-Benzyloxymethyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of pyrazole (4.92 g, 72.2 mmol) in THF (100 mL) at −78° C. is added n-BuLi (28.9 mL of 2.5M in hexane) dropwise. The mixture is warmed to RT then re-cooled to −78° C. then Bom-Cl (11.3 g, 72.2 mmol) is added and the mixture is allowed to warm to RT. The solvent is removed under reduced pressure and 1N NaOH (25 mL) is added to the residual solid. The mixture is extracted with ether and the organic phase is washed with brine and dried over sodium sulfate. The solvent is removed under reduced pressure and the residue purified by reverse phase-MPLC using a gradient of 25-50% MeCN/water as eluent to give the title compound.

Workup

  1. temperaturethen re-cooled to −78° C.
  2. temperatureto warm to RT
  3. customThe solvent is removed under reduced pressure and 1N NaOH (25 mL)
  4. additionis added to the residual solid
  5. extractionThe mixture is extracted with ether
  6. washthe organic phase is washed with brine
  7. dry with materialdried over sodium sulfate
  8. customThe solvent is removed under reduced pressure
  9. customthe residue purified by reverse phase-MPLC

Sources & evidence

ORD record
ord-53fa883a7a51459fa30aa7bd3b115901
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

Loading…