반응 #2139936

반응 방정식

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

용매

water

THF

반응 조건

후처리

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

실험 절차

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).

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