반응 #3036

반응 방정식

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

수율 71.0%

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

수율 71.0%

용매

toluene

반응 조건

후처리

1. 1
   온도at reflux temperature for one hour
2. 2
   기타The product was isolated
3. 3
   기타to the cooled reaction mixture
4. 4
   기타separating the layers
5. 5
   세척washing the organic layer with 1N hydrochloric acid
6. 6
   건조a saturated sodium chloride solution, drying over magnesium sulfate
7. 7
   농축concentrating in vacuo
8. 8
   기타purifying the residue by chromatography over silica gel eluting with a 10-50% hexane in ethyl acetate gradient

실험 절차

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.

출처