反应 #2139937

反应方程式

2,2,2-Trifluoro-1-(4-methoxyphenyl)-ethanone oxime

2-chloroethanesulfonyl chloride

triethylamine

p-toluenesulfinic acid sodium salt

→

product

2,2,2-trifluoro-1-(4-methoxyphenyl)-ethanone oxime 2-(p-toluene-sulfonyl)-ethanesulfonate

溶剂

THF

water

dimethylformamide

反应条件

后处理

1. 1
   温度the solution is cooled in an ice-bath
2. 2
   workup.STIRRINGthe reaction solution is stirred at room temperature for 0.5 h
3. 3
   萃取the crude product is extracted with ethyl acetate twice
4. 4
   洗涤washed with water
5. 5
   干燥dried over MgSO4
6. 6
   浓缩concentrated
7. 7
   其他The residue is purified by recrystallization from ethanol/toluene

实验过程

In 40 mL of THF are dissolved 4.38 g (20.0 mmol) of 2,2,2-Trifluoro-1-(4-methoxyphenyl)-ethanone oxime and the solution is cooled in an ice-bath. To the solution are added successively 2-chloroethanesulfonyl chloride (2.3 mL, 22.0 mmol) and triethylamine (6.4 mL, 46.0 mmol), and the reaction solution is stirred at 0° C. for 1 h. Then, p-toluenesulfinic acid sodium salt (3.56 g, 20.0 mmol) in dimethylformamide (DMF) (80 mL) is added and the reaction solution is stirred at room temperature for 0.5 h. After the reaction mixture is poured into water, the crude product is extracted with ethyl acetate twice, washed with water, dried over MgSO4 and concentrated. The residue is purified by recrystallization from ethanol/toluene to afford the product as white solid. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 2.49 (s, 3H), 3.53 (t, 2H), 3.77 (t, 2H), 3.88 (s, 3H), 7.00 (d, 2H), 7.42 (d, 2H), 7.50 (d, 2H), 7.80 (d, 2H). mp. 157-158° C.

来源