Isobutylene oxide → 2-methyl-1-(3-nitro-1H-pyrazol-1-yl)propan-2-ol

Participants

Reaction Conditions

Reaction Steps

A solution of 3-nitro-1H-pyrazole (200 mg, 1.77 mmol) in N,N-dimethylformamide (5 mL) was treated with solid potassium carbonate (352 mg, 2.55 mmol) and 2,2-dimethyl-oxirane (3.14 mL, 3.54 mmol) and placed in a sealed tube and heated at 100° C. for 1 h in an oil bath. After this time the reaction was cooled to 25° C. and diluted with water (10 mL) and extracted with ethyl acetate (3×10 mL). The organic layers were then combined and dried over sodium sulfate, filtered and concentrated in vacuo. Purification by AnaLogix Intelliflash system (12 g column, 50% ethyl acetate/hexanes to 60% ethyl acetate/hexanes) afforded 2-methyl-1-(3-nitro-pyrazol-1-yl)-propan-2-ol (175 mg, 54%) as a clear colorless oil: ES-HRMS m/z calculated for C7H11N3O3 [M+H]+ 186.0873, observed 186.0873; 1H NMR (300 MHz, CDCl3) δ ppm 1.25 (s, 6H), 2.11 (br. s., 1H), 4.18 (s, 2H), 6.92 (d, J=2.4 Hz, 1H), 7.60 (d, J=2.4 Hz, 1H).

Provenance & Evidence