反应 #3039

反应方程式

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

收率 59.7%

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

收率 59.7%

溶剂

toluene

反应条件

后处理

1. 1
   温度the solution heated
2. 2
   温度at reflux temperature for an additional 10 minutes
3. 3
   温度After cooling
4. 4
   洗涤the mixture was washed with 1.25l of 1N hydrochloric acid
5. 5
   其他a precipitate separated
6. 6
   其他The liquid portion was decanted off
7. 7
   其他the resulting residue was purified by chromatography over silica gel
8. 8
   洗涤eluting with a gradient of 25-50% of ethyl acetate in hexane
9. 9
   浓缩concentrated in vacuo

实验过程

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.

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