反応 #792139

反応方程式

sodium hydride

trimethylsulfonium iodide

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

→

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

収率 107.5%

溶媒

THF

DMSO

DMSO

DMSO

反応条件

後処理

1. 1
   温度The resulting mixture was then warmed to room temperature overnight
2. 2
   その他quenched with an aqueous solution of ammonium chloride and iced water
3. 3
   抽出extracted with MTBE
4. 4
   洗浄The organic solvents were washed with water
5. 5
   その他dried
6. 6
   その他evaporated

実験手順

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).

出典