Reacción #944013

Ecuación de reacción

ammonium chloride

potassium t-butoxide

methyl cyanoacetate

4-methylthiophenacyl bromide

→

title compound

Rendimiento 21.8%

Methyl 2-(4-methylthiophenacyl)cyanoacetate

Rendimiento 21.8%

Disolventes

ethyl acetate

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   Temperaturacooling
3. 3
   workup.STIRRINGThe mixture was stirred, whilst ice-
4. 4
   Temperaturacooling for 2 hours
5. 5
   FiltraciónThe insolubles were then filtered off
6. 6
   workup.ADDITIONWater was added to the filtrate
7. 7
   Extracciónthe mixture was extracted with ethyl acetate
8. 8
   ExtracciónThe organic extract
9. 9
   Secadowas dried over anhydrous magnesium sulfate
10. 10
    Otrothe solvent was then removed by distillation under reduced pressure
11. 11
    Lavadoeluted with a 1:2 by volume mixture of ethyl acetate and hexane

Procedimiento

5.70 g (57.6 mmol) of methyl cyanoacetate were dissolved in 150 ml of anhydrous tetrahydrofuran, and 7.10 g (63.3 mmol) of potassium t-butoxide were added to the resulting solution, whilst ice-cooling, and the mixture was then stirred for 30 minutes. At the end of this time, a solution of 14.11 g (57.6 mmol) of 4-methylthiophenacyl bromide in 50 ml of tetrahydrofuran was slowly added dropwise to the mixture, whilst ice-cooling. The mixture was stirred, whilst ice-cooling for 2 hours, and then a saturated aqueous solution of ammonium chloride and ethyl acetate were added. The insolubles were then filtered off. Water was added to the filtrate, and the mixture was extracted with ethyl acetate. The organic extract was dried over anhydrous magnesium sulfate and the solvent was then removed by distillation under reduced pressure. The residue was applied to a silica gel chromatography column and eluted with a 1:2 by volume mixture of ethyl acetate and hexane, to give 3.11 g (yield 21%) of the title compound as a slightly yellow powder.

Fuente