Reacción #2139936

Ecuación de reacción

2-chloroethanesulfonyl chloride

triethylamine

1-butanethiol

triethylamine

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

→

product

2,2,2-trifluoro-1-(4-methoxyphenyl)-ethanone oxime 2-(n-butylthio)-ethanesulfonate

Disolventes

water

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe solution is cooled in an ice-bath
2. 2
   workup.STIRRINGthe reaction solution is stirred at room temperature for 0.5 h
3. 3
   Extracciónthe crude product is extracted with ethyl acetate twice
4. 4
   Lavadowashed with water
5. 5
   Secadodried over MgSO4
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe residue is purified by column chromatography on silica gel with hexane—ethyl acetate (10:1 to 5:1) as an eluent

Procedimiento

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, 1-butanethiol (2.4 mL, 22.0 mmol) and triethylamine (4.2 mL, 30.0 mmol) are added successively, 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 column chromatography on silica gel with hexane—ethyl acetate (10:1 to 5:1) as an eluent to afford the product as yellow oil. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 0.92 (t, 3H), 1.41 (m, 2H), 1.57 (m, 2H), 2.56 (t, 2H), 2.93 (t, 2H), 3.66 (t, 2H), 3.87 (s, 3H), 7.00 (d, 2H), 7.55 (d, 2H).

Fuente