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

HRID 1903901Notes

Reaction equation

HRID 1903901 reaction equation
[O:1]1[CH2:12][CH:2]1[CH2:3][P:4](=[O:11])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7].[NH:13]1[CH:17]=[N:16][CH:15]=[N:14]1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[OH:1][CH:2]([CH2:12][N:13]1[CH:17]=[N:16][CH:15]=[N:14]1)[CH2:3][P:4](=[O:11])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 98446Diethyl 2,3-epoxypropylphosphonate

Product 1

HCID 13209641Diethyl 2-hydroxy-3(1,2,4-triazol-1-yl)propylphosphonateYield 38%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

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.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for four hours
  3. customThe supernatant liquid was decanted from a sticky residue
  4. customevaporated under reduced pressure
  5. customThe crude product was purified by preparative high performance liquid chromatography (

Sources & evidence

ORD record
ord-83c2b78b64df437ba496f8de2b34e71e
Source dataset
uspto-grants-1984_03
Patent number
US04439428

Reaction notes

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