反応 #2139936

反応方程式

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

溶媒

water

THF

反応条件

後処理

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
   抽出the crude product is extracted with ethyl acetate twice
4. 4
   洗浄washed with water
5. 5
   乾燥dried over MgSO4
6. 6
   濃縮concentrated
7. 7
   その他The residue is purified by column chromatography on silica gel with hexane—ethyl acetate (10:1 to 5:1) as an eluent

実験手順

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).

出典