Réaction #3036

Équation de réaction

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

Rendement 71.0%

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

Rendement 71.0%

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   Températureat reflux temperature for one hour
2. 2
   AutreThe product was isolated
3. 3
   Autreto the cooled reaction mixture
4. 4
   Autreseparating the layers
5. 5
   Lavagewashing the organic layer with 1N hydrochloric acid
6. 6
   Séchagea saturated sodium chloride solution, drying over magnesium sulfate
7. 7
   Concentrationconcentrating in vacuo
8. 8
   Autrepurifying the residue by chromatography over silica gel eluting with a 10-50% hexane in ethyl acetate gradient

Mode opératoire

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.

Source