تفاعل #3036

معادلة التفاعل

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

المردود 71.0%

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

المردود 71.0%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةat reflux temperature for one hour
2. 2
   أخرىThe product was isolated
3. 3
   أخرىto the cooled reaction mixture
4. 4
   أخرىseparating the layers
5. 5
   غسيلwashing the organic layer with 1N hydrochloric acid
6. 6
   تجفيفa saturated sodium chloride solution, drying over magnesium sulfate
7. 7
   تركيزconcentrating in vacuo
8. 8
   أخرىpurifying the residue by chromatography over silica gel eluting with a 10-50% hexane in ethyl acetate gradient

الإجراء التجريبي

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.

المصدر