反応 #3039

反応方程式

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

収率 59.7%

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

収率 59.7%

溶媒

toluene

反応条件

後処理

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
   洗浄the mixture was washed with 1.25l of 1N hydrochloric acid
5. 5
   その他a precipitate separated
6. 6
   その他The liquid portion was decanted off
7. 7
   その他the resulting residue was purified by chromatography over silica gel
8. 8
   洗浄eluting with a gradient of 25-50% of ethyl acetate in hexane
9. 9
   濃縮concentrated in vacuo

実験手順

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.

出典