تفاعل #3039

معادلة التفاعل

5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-[2-(acetyloxy) ethyl]-2-thioxo-4-thiazolidinone

Tri-n-butyl tin hydride

AIBN

→

desired titled compound

المردود 59.7%

5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-[2-(acetyloxy)ethyl]-4-thiazolidinone

المردود 59.7%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe solution heated
2. 2
   درجة الحرارةat reflux temperature for an additional 10 minutes
3. 3
   درجة الحرارةAfter cooling
4. 4
   غسيلthe mixture was washed with 1.25l of 1N hydrochloric acid
5. 5
   أخرىa precipitate separated
6. 6
   أخرىThe liquid portion was decanted off
7. 7
   أخرىthe resulting residue was purified by chromatography over silica gel
8. 8
   غسيلeluting with a gradient of 25-50% of ethyl acetate in hexane
9. 9
   تركيزconcentrated in vacuo

الإجراء التجريبي

Under a nitrogen atmosphere, 82.2 g of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-[2-(acetyloxy) ethyl]-2-thioxo-4-thiazolidinone in 950 ml of toluene was heated to 65° C. Tri-n-butyl tin hydride (219.7 g) and AIBN (4.65 g) were added and the solution heated at reflux temperature for an additional 10 minutes. After cooling, the mixture was washed with 1.25l of 1N hydrochloric acid followed by 500 ml of a saturated sodium chloride solution. The organic layer was stripped and allowed to stand overnight, during which time a precipitate separated. The liquid portion was decanted off, and the resulting residue was purified by chromatography over silica gel, eluting with a gradient of 25-50% of ethyl acetate in hexane. The appropriate fractions were combined and concentrated in vacuo to provide 45.7 g of the desired titled compound, m.p.=152°-155° C.

المصدر