反応 #3036

反応方程式

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

収率 71.0%

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

収率 71.0%

溶媒

toluene

反応条件

後処理

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

実験手順

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.

出典