Реакция #792139

Уравнение реакции

sodium hydride

trimethylsulfonium iodide

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

→

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

Выход 107.5%

Растворители

THF

DMSO

DMSO

DMSO

Условия реакции

Обработка

1. 1
   ТемператураThe resulting mixture was then warmed to room temperature overnight
2. 2
   Другоеquenched with an aqueous solution of ammonium chloride and iced water
3. 3
   Экстракцияextracted with MTBE
4. 4
   ПромывкаThe organic solvents were washed with water
5. 5
   Другоеdried
6. 6
   Другоеevaporated

Методика

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).

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