反应 #3036

反应方程式

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

收率 71.0%

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

收率 71.0%

溶剂

toluene

反应条件

后处理

1. 1
   温度at reflux temperature for one hour
2. 2
   其他The product was isolated
3. 3
   其他to the cooled reaction mixture
4. 4
   其他separating the layers
5. 5
   洗涤washing the organic layer with 1N hydrochloric acid
6. 6
   干燥a saturated sodium chloride solution, drying over magnesium sulfate
7. 7
   浓缩concentrating in vacuo
8. 8
   其他purifying the residue by chromatography over silica gel eluting with a 10-50% hexane in ethyl acetate gradient

实验过程

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.

来源