Reacción #6786

Ecuación de reacción

4-methylbenzenethiol

NaH

Ethylbromoacetate

→

colorless oil

Rendimiento 99.0%

p-Tolylsulfanyl-acetic acid ethyl ester

Rendimiento 99.0%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente