Allyl Alcohol → 1-(2-(allyloxy)-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole

Participants

Reaction Conditions

Reaction Steps

A suspension of NaH (2.295 g 57.4 mmol, 60% dispersion in mineral oil) in DMF (85 mL) was cooled at 0° C. and a solution 1-(2-fluoro-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole (8.50 g 38.3 mmol) was added dropwise. Allyl alcohol (2.67 g, 49.9 mmol) was added via syringe over 10 min. The reaction mixture was allowed to warm to room temperature. After 30 min, TLC showed completion of reaction. The reaction mixture was slowly quenched with water (20 mL), treated with 200 mL of brine and extracted with EtOAc (3×200 mL). The combined organic extracts were washed with water (3×200 mL) and brine solution (100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude reaction mixture was purified using silica gel chromatography (20-80% EtOAc/hexane, linear gradient). Pure fractions were concentrated under reduced pressure to afford 1-(2-(allyloxy)-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole (5 g, 19.21 mmol 50% yield) as a yellow colored solid. LC-MS (M+H)+=261.0. 1H NMR (400 MHz, CDCl3) δ ppm 8.906 (s, 1H), 8.09 (d, 1H, J=8.8 Hz), 7.99-7.94 (m, 2H), 6.13-6.03 (m, 1H), 5.50-5.54 (m, 2H), 4.80-4.79 (m, 2H), 2.497 (s, 3H).

Provenance & Evidence