1H-1,2,4-Triazole → HCID 18406943, compound

Participants

Reaction Steps

To a solution of [1,2,4]triazole (7.3 g, 0.11 mol), triphenylphosphine (33 g, 0.13 mol) and 2,2-difluoroethanol (8.0 ml, 10 g, 0.13 mol) in THF (115 ml) was added diethyl azodicarboxylate (20 ml, 22 g, 0.13 mol) dropwise, maintaining the temperature of the mixture between −5 and 0° C. throughout the addition. The resultant solution was allowed to warm to room temperature and was stirred under nitrogen overnight. The solvent was removed it uacuo, and diethyl ether (220 ml) was added to the residue, precipitating a solid. This was separated by filtration, and the filtrate was concentrated in vacuo. The residual oil was purified by distillation under vacuum, yielding 1-(2,2-difluoroethyl)-1H-[1,2,4]triazole as a yellow oil (7.1 g). Data for the title compound: 1H NMR (250 MHz, CDCl3) δ 4.56 (2H, td, J=13.5, 4.1 Hz), 6.13 (1H, tt, J=55.1, 4.2 Hz), 8.01 (1H, s), 8.18 (1H, s).

Provenance & Evidence