Реакция #6786

Уравнение реакции

4-methylbenzenethiol

NaH

Ethylbromoacetate

→

colorless oil

Выход 99.0%

p-Tolylsulfanyl-acetic acid ethyl ester

Выход 99.0%

Растворители

THF

THF

Условия реакции

Обработка

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

Методика

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).

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