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ChemicalBook CAS DataBase List 5-(Hydroxymethyl)-1-methyl-1H-pyrazole

5-(Hydroxymethyl)-1-methyl-1H-pyrazole synthesis

4synthesis methods
-

Yield: 83.3%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 0 - 20; for 12 h;

Steps:

1.2 Step 2: (l-methyl-lH-pyrazol-5-yl)methanol
To a stirred solution of methyl l-methyl-lH-pyrazole-5-carboxylate (3 g, 21.4 mmol) in tetrahydrofuran (50 mL) at 0 °C was added lithium aluminum hydride (977 mg, 25.7 mmol). The mixture was stirred at room temperature for 12 h. The reaction was quenched by adding water, extracted with ethyl acetate (100 mL), dried, concentrated and the residue was purified by column chromatography on silica gel (petroleum ether/ acetic ester =10: 1), to afford the title compound as an off-white oil (2 g, 83.3%).

References:

CONSTELLATION PHARMACEUTICALS, INC.;ALBRECHT, Brian, K.;AUDIA, James, Edmund;COOK, Andrew;COTE, Alexandre;DAKIN, Les, A.;GEHLING, Victor, S.;HARMANGE, Jean-Christophe;NASVESCHUK, Christopher, G.;VASWANI, Rishi, G. WO2014/151142, 2014, A1 Location in patent:Paragraph 0093