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 (Intermediate 2, 200 mg, 1.77 mmol) in N,N-dimethylformamide (5 mL) was treated with potassium carbonate (352 mg, 2.55 mmol) and 1,1-dimethyloxirane (314 mL, 3.54 mmol) and placed in a sealed tube and heated to 100° C. for 1 h. After this time, the reaction was cooled to 25° C., 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. Silica gel column chromatography (AnaLogix, 12 g column, 50-60% 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/e calcd 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