تفاعل #6786

معادلة التفاعل

4-methylbenzenethiol

NaH

Ethylbromoacetate

→

colorless oil

المردود 99.0%

p-Tolylsulfanyl-acetic acid ethyl ester

المردود 99.0%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر