反应 #6786

反应方程式

4-methylbenzenethiol

NaH

Ethylbromoacetate

→

colorless oil

收率 99.0%

p-Tolylsulfanyl-acetic acid ethyl ester

收率 99.0%

溶剂

THF

THF

反应条件

后处理

1. 1
   workup.STIRRINGfurther stirred at room temperature for 3 h
2. 2
   其他The solvent was removed under vacuum
3. 3
   workup.DISSOLUTIONThe residue was dissolved in oil
4. 4
   萃取HCl and extracted by ethylacetate
5. 5
   洗涤The combined organic phase was washed successively with saturated NaHCO3 solution, water and brine
6. 6
   干燥then dried over Na2SO4
7. 7
   其他Evaporation of organic phase

实验过程

A solution of 4-methylbenzenethiol (5 g, 40.25) in dry THF was added dropwise to a suspension of NaH (60% in mineral oil, 1.98 g, 48.30) in THF at room temperature and stirred for 30 min. under N2 atmosphere. Ethylbromoacetate (4.9 mL, 44.27) was added slowly to this solution and further stirred at room temperature for 3 h. The solvent was removed under vacuum. The residue was dissolved in oil. HCl and extracted by ethylacetate. The combined organic phase was washed successively with saturated NaHCO3 solution, water and brine then dried over Na2SO4. Evaporation of organic phase yielded 8.46 g (99%) colorless oil. 1H NMR (CDCl3): δ 1.22 (t, J=7.2 Hz, 3H), 2.32 (s, 3H), 3.57 (s, 2H), 4.14 (q, J=7.2 Hz, 2H), 7.11 (d, J=8.0 Hz, 2H), 7.33 (d, J=8.0 Hz, 2H). EIMS m/z 210 (M+1), 233 (M+23).

来源