Reacción #6433

Ecuación de reacción

1-methyl-1,2,4-triazole

diethyl 3-oxo-butylphosphonate

→

diethyl 3-hydroxy-3-methyl-3-(1-methyl-1,2,4-triazol-5-yl)propyl-phosphonate

Rendimiento 28.4%

Disolventes

tetrahydrofurane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was stirred for 2 hours
2. 2
   Otroquenched with aq. NH4Cl (ca. 15 ml)
3. 3
   Extracciónextracted with CH2Cl2 (5×100 ml)
4. 4
   SecadoThe extract was dried over MgSO4
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   Otropurified by a silica gel column chromatography (200 g, AcOEt-EtOH)

Procedimiento

To a solution of 1-methyl-1,2,4-triazole (3.0 g, 36.1 mmol) in tetrahydrofurane (60 ml) was added n-buthyllithium (43.3 mmol, 1.2 eq) at -78° C. under nitrogen. The mixture was stirred for 1 hour, then diethyl 3-oxo-butylphosphonate (8.3 g, 39.7 mmol, 1.1 eq) was added. The mixture was stirred for 2 hours and quenched with aq. NH4Cl (ca. 15 ml). The mixture was warmed to room temperature and extracted with CH2Cl2 (5×100 ml). The extract was dried over MgSO4, concentrated in vacuo, and purified by a silica gel column chromatography (200 g, AcOEt-EtOH) to give (2.99 g, 28% yield) of diethyl 3-hydroxy-3-methyl-3-(1-methyl-1,2,4-triazol-5-yl)propyl-phosphonate.

Fuente