Reacción #792138

Ecuación de reacción

ethanone

1-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-2-[1,2,4]triazol-1-ylethanone

1-propynylmagnesium bromide

→

title compound

2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)pent-3-yn-2-ol

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe resulting mixture was quenched with a 10% aqueous solution of HCl
2. 2
   Extracciónextracted with MTBE
3. 3
   LavadoThe organic phase was washed with brine
4. 4
   Otrodried
5. 5
   Otroevaporated
6. 6
   Filtraciónfiltrated
7. 7
   OtroThe mother liquors were evaporated
8. 8
   Otropurified on silica gel

Procedimiento

To a solution of the above-mentioned ethanone (75.5 g, 216.8 mmol) dissolved in THF (450 mL) was added a solution of LaCl3.2LiCl (395.9 mL, 0.6 M in THF) at room temperature and stirred for 1 hour. The resulting solution was added dropwise to 1-propynylmagnesium bromide (650.5 mL, 0.5M in THF) at room temperature. After 1 hour at room temperature, the resulting mixture was quenched with a 10% aqueous solution of HCl and extracted with MTBE. The organic phase was washed with brine, dried and evaporated. The crude compound was stirred in a solution of MTBE/diisopropylether and filtrated to eliminate the starting material. The mother liquors were evaporated and purified on silica gel to give the title compound as a beige solid (31.1 g, HPLC-MS2 Rt=1.15 min, masse=388, m.p=137° C.).

Fuente