Reacción #792139

Ecuación de reacción

sodium hydride

trimethylsulfonium iodide

1-[2-chloro-4-(4-chlorophenoxy)phenyl]propan-1-one

→

2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-ethyl-oxirane

Rendimiento 107.5%

Disolventes

THF

DMSO

DMSO

DMSO

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe resulting mixture was then warmed to room temperature overnight
2. 2
   Otroquenched with an aqueous solution of ammonium chloride and iced water
3. 3
   Extracciónextracted with MTBE
4. 4
   LavadoThe organic solvents were washed with water
5. 5
   Otrodried
6. 6
   Otroevaporated

Procedimiento

To a solution of sodium hydride (35.72 g, 1.49 mol) in THF (1 L) and dry DMSO (2 L) was added under argon drop wise at 5° C. a solution of trimethylsulfonium iodide (290.5 g, 1.42 mol) in dry DMSO (2 L). The mixture was stirred 1 hour at 5° C. followed by a dropwise addition of 1-[2-chloro-4-(4-chlorophenoxy)phenyl]propan-1-one (199.0 g, 0.65 mol) in DMSO (500 mL). The resulting mixture was then warmed to room temperature overnight and quenched with an aqueous solution of ammonium chloride and iced water, and then extracted with MTBE. The organic solvents were washed with water, dried and evaporated to give 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-ethyl-oxirane as a yellowish solid (216.0 g, 97%). 1H-NMR (CDCl3; 400 MHz) • • (ppm)=0.9 (t, 3H); 1.75 (m, 1H); 2.10 (m, 1H); 2.80 (d, 1H); 3.05 (d, 1H); 6.85 (d, 1H); 6.95 (m, 3H); 7.30 (d, 2H); 7.40 (d, 1H).

Fuente