1H-1,2,4-Triazole → Diethyl 2-hydroxy-3(1,2,4-triazol-1-yl)propylphosphonate

Participants

Reaction Steps

A mixture of diethyl 2,3-epoxypropylphosphonate (14.55 g), 1,2,4-triazole (5.18 g), potassium carbonate (10.35 g) and methyl ethyl ketone (220 ml) was heated under reflux for four hours. The supernatant liquid was decanted from a sticky residue and evaporated under reduced pressure. The crude product was purified by preparative high performance liquid chromatography (using a Waters LC 500 apparatus, silica as solid phase, and ethanol: ether in the proportion of 1:2 by volume as the liquid phase) to give diethyl 2-hydroxy-3(1,2,4-triazol-1-yl)propylphosphonate (7.5 g) as a pale yellow viscous oil. The identity of the product was confirmed by examination of its infra-red; mass; and proton, P31 and C13 nuclear magnetic resonance spectra, which were all consistent with the structure assigned.

Provenance & Evidence