Potassium Carbonate → Dimethyl 1-[2-(2-methoxyethoxy)ethyl]-4-nitro-1H-pyrazole-3,5-dicarboxylate

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Reaction Conditions

Reaction Steps

Dimethyl 4-nitro-1H-pyrazole-3,5-dicarboxylate (9.53 g, 41.6 mmol) and potassium carbonate (3.44 g, 25 mmol) were dissolved in N,N-dimethylformamide (140 mL) under nitrogen. The mixture was then treated with a solution of 1-bromo-2-(2-methoxyethoxy)ethane (9.90 g, 54 mmol) in N,N-dimethylformamide (10 mL). The reaction mixture was stirred at 30° C. for 18 hours and then allowed to cool to room temperature. Additional 1-bromo-2-(2-methoxyethoxy)ethane (9.90 g, 54 mmol) and potassium carbonate (3.44 g, 25 mmol) were added and the reaction mixture allowed to stir at 30° C. for 4 hours. The reaction mixture was concentrated in vacuo and the residue taken up in ethyl acetate (200 mL) and water (200 mL). The aqueous was separated and washed with ethyl acetate (200 mL), the organics were combined and washed with water. The organic layer was dried over magnesium sulphate and concentrated in vacuo to yield the title product. 1H NMR (CDCl3, 400 MHz) δ: 3.25 (s, 3H), 3.38 (m, 2H), 3.50 (m, 2H), 3.80 (t, 2H), 3.92 (s, 3H), 3.93 (s, 3H), 4.77 (t, 2H). MS APCI+ m/z 333 [MH]+

Provenance & Evidence