Reacción #3036

Ecuación de reacción

tri-n-butyl tin hydride

azobisisobutyronitrile

water

thione

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

→

title compound

Rendimiento 71.0%

5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-methyl-4-thiazolidinone

Rendimiento 71.0%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux temperature for one hour
2. 2
   OtroThe product was isolated
3. 3
   Otroto the cooled reaction mixture
4. 4
   Otroseparating the layers
5. 5
   Lavadowashing the organic layer with 1N hydrochloric acid
6. 6
   Secadoa saturated sodium chloride solution, drying over magnesium sulfate
7. 7
   Concentraciónconcentrating in vacuo
8. 8
   Otropurifying the residue by chromatography over silica gel eluting with a 10-50% hexane in ethyl acetate gradient

Procedimiento

The title compound was prepared in 71% yield from 10.31 g of the thione of Example 9 upon heating with 38.15 ml of tri-n-butyl tin hydride and 1.16 g of azobisisobutyronitrile (AIBN) in 142 ml of toluene at reflux temperature for one hour. The product was isolated by adding water to the cooled reaction mixture, separating the layers, washing the organic layer with 1N hydrochloric acid and a saturated sodium chloride solution, drying over magnesium sulfate, concentrating in vacuo, and purifying the residue by chromatography over silica gel eluting with a 10-50% hexane in ethyl acetate gradient. The purified product had a melting point of 142°-144° C.

Fuente