反応 #2195491

反応方程式

4-methylbenzenethiol

NaH

Ethylbromoacetate

→

colorless oil

収率 99.0%

p-Tolylsulfanyl-acetic acid ethyl ester

収率 99.0%

溶媒

THF

THF

反応条件

後処理

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

実験手順

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 dil. 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).

出典