Cesium carbonate → HCID 69380447, compound

Participants

Reaction Conditions

Reaction Steps

4-(4-Methoxy-phenyl)-5-methyl-1H-pyrazole (1 eq) was taken up in DMF and under N2 was cooled to 0° C. Caesium carbonate (1 eq) was added and the solution was stirred for five minutes. 2-(Trimethylsilyl)ethoxy methyl chloride (0.95 eq) was added dropwise and all was stirred for 2 hours. The reaction mixture was partitioned between water and EtOAc. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to give a gum. This was purified by flash chromatography (8:1 hexane: EtOAc) to give 4-(4-methoxy-phenyl)-5-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazole and 4-(4-methoxy-phenyl)-3-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazole as a mixture of isomers.

Provenance & Evidence