Pyrazole → 1-Benzyloxymethyl-1H-pyrazole

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Reaction Steps

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.

Provenance & Evidence