Reacción #49731

Ecuación de reacción

Hydrochloric acid

Cyclopropyl methyl ketone

sodium hydride

ethyl 4-(methylsulphenyl)benzoate

→

3-cyclopropyl-1-[4-(methylsulphenyl)-phenyl]-propan-1,3-dione

Rendimiento 49.4%

Disolventes

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was stirred
2. 2
   workup.WAITIt was left
3. 3
   workup.WAITto stand at room temperature overnight
4. 4
   Extracciónthe mixture was extracted with ethyl acetate
5. 5
   Lavadowashed with water
6. 6
   Secadodried (MgSO4)
7. 7
   Filtraciónfiltered
8. 8
   OtroThe flitrate was evaporated to dryness
9. 9
   Otrothe residue was purified by chromatography
10. 10
    Lavadoeluted with a mixture of ethyl acetate and hexane

Procedimiento

Cyclopropyl methyl ketone (0.84 g) was added to a suspension of sodium hydride (80%, 0.3 g) in dioxane. The mixture was stirred for 20 minutes and ethyl 4-(methylsulphenyl)benzoate (1.0 g) was added. The mixture was stirred and heated at 45° C. for 1.5 hours and at 60° C. for 2 hours. It was left to stand at room temperature overnight. Hydrochloric acid (2M) was added and the mixture was extracted with ethyl acetate, washed with water, dried (MgSO4) and filtered. The flitrate was evaporated to dryness and the residue was purified by chromatography eluted with a mixture of ethyl acetate and hexane to give 3-cyclopropyl-1-[4-(methylsulphenyl)-phenyl]-propan-1,3-dione (0.59 g) as an orange solid, NMR (CDCl3) 1.0(m,2H), 1.2(m,2H), 1.8(m, 1H), 2.5(s,3H), 6.25(s,1H), 7.25(d,2H), 7.8(d,2H), 16.35(bs,1H).

Fuente