Ammonia → 3-(Methoxymethyl)-1-methyl-4-nitropyrazole

Participants

Reaction Steps

(1-Methyl-4-nitropyrazol-3-yl)methanol (2.0 g) was dissolved in THF (80 ml) and NaH (0.6 g, 60% in oil) added at <5° C. After 30 minutes, dimethylsulfate (1.92 g) was added and the reaction stirred overnight at room temperature. An additional 0.5 eq NaH was charged and the reaction warmed to 50° C. for 30 minutes. The reaction was cooled to room temperature, and water added dropwise (10 ml), then the mixture was poured into 5% aq. ammonia (100 ml). The organic phase was separated and the aqueous extracted with EtOAc (4×50 ml). The combined organic phases were washed with 5% aq. ammonia (2×50 ml), brine (50 ml), then dried, filtered and concentrated in vacuo to yield 3-(methoxymethyl)-1-methyl-4-nitropyrazole, 2.03 g, 94%.

Provenance & Evidence