반응 #6786

반응 방정식

4-methylbenzenethiol

NaH

Ethylbromoacetate

→

colorless oil

수율 99.0%

p-Tolylsulfanyl-acetic acid ethyl ester

수율 99.0%

용매

THF

THF

반응 조건

후처리

1. 1
   workup.STIRRINGfurther stirred at room temperature for 3 h
2. 2
   기타The solvent was removed under vacuum
3. 3
   workup.DISSOLUTIONThe residue was dissolved in oil
4. 4
   추출HCl and extracted by ethylacetate
5. 5
   세척The combined organic phase was washed successively with saturated NaHCO3 solution, water and brine
6. 6
   건조then dried over Na2SO4
7. 7
   기타Evaporation of organic phase

실험 절차

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).

출처