Chloromethyl Methyl Ether → 4-ethyl 1-tert-butyl 3-(methoxymethoxy)-1H-pyrazole-1,4-dicarboxylate

Participants

Reaction Steps

A mixture of 4-ethyl 1-tert-butyl 3-hydroxy-1H-pyrazole-1,4-dicarboxylate (30.75 g), chloromethyl methyl ether (4.56 mL), N,N-diisopropylethylamine (11.9 mL) and tetrahydrofuran (150 mL) was stirred at room temperature for 2 hrs. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:9-1:2, v/v) to give 4-ethyl 1-tert-butyl 3-(methoxymethoxy)-1H-pyrazole-1,4-dicarboxylate as a pale-yellow oil (3.52 g, yield 20%).

Provenance & Evidence