Reacción #3039

Ecuación de reacción

5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-[2-(acetyloxy) ethyl]-2-thioxo-4-thiazolidinone

Tri-n-butyl tin hydride

AIBN

→

desired titled compound

Rendimiento 59.7%

5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-[2-(acetyloxy)ethyl]-4-thiazolidinone

Rendimiento 59.7%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe solution heated
2. 2
   Temperaturaat reflux temperature for an additional 10 minutes
3. 3
   TemperaturaAfter cooling
4. 4
   Lavadothe mixture was washed with 1.25l of 1N hydrochloric acid
5. 5
   Otroa precipitate separated
6. 6
   OtroThe liquid portion was decanted off
7. 7
   Otrothe resulting residue was purified by chromatography over silica gel
8. 8
   Lavadoeluting with a gradient of 25-50% of ethyl acetate in hexane
9. 9
   Concentraciónconcentrated in vacuo

Procedimiento

Under a nitrogen atmosphere, 82.2 g of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-[2-(acetyloxy) ethyl]-2-thioxo-4-thiazolidinone in 950 ml of toluene was heated to 65° C. Tri-n-butyl tin hydride (219.7 g) and AIBN (4.65 g) were added and the solution heated at reflux temperature for an additional 10 minutes. After cooling, the mixture was washed with 1.25l of 1N hydrochloric acid followed by 500 ml of a saturated sodium chloride solution. The organic layer was stripped and allowed to stand overnight, during which time a precipitate separated. The liquid portion was decanted off, and the resulting residue was purified by chromatography over silica gel, eluting with a gradient of 25-50% of ethyl acetate in hexane. The appropriate fractions were combined and concentrated in vacuo to provide 45.7 g of the desired titled compound, m.p.=152°-155° C.

Fuente