Реакция #3036

Уравнение реакции

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

Выход 71.0%

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

Выход 71.0%

Растворители

toluene

Условия реакции

Обработка

1. 1
   Температураat reflux temperature for one hour
2. 2
   ДругоеThe product was isolated
3. 3
   Другоеto the cooled reaction mixture
4. 4
   Другоеseparating the layers
5. 5
   Промывкаwashing the organic layer with 1N hydrochloric acid
6. 6
   Сушкаa saturated sodium chloride solution, drying over magnesium sulfate
7. 7
   Концентрированиеconcentrating in vacuo
8. 8
   Другоеpurifying the residue by chromatography over silica gel eluting with a 10-50% hexane in ethyl acetate gradient

Методика

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.

Источник