Réaction #3039

Équation de réaction

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

Rendement 59.7%

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

Rendement 59.7%

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   Températurethe solution heated
2. 2
   Températureat reflux temperature for an additional 10 minutes
3. 3
   TempératureAfter cooling
4. 4
   Lavagethe mixture was washed with 1.25l of 1N hydrochloric acid
5. 5
   Autrea precipitate separated
6. 6
   AutreThe liquid portion was decanted off
7. 7
   Autrethe resulting residue was purified by chromatography over silica gel
8. 8
   Lavageeluting with a gradient of 25-50% of ethyl acetate in hexane
9. 9
   Concentrationconcentrated in vacuo

Mode opératoire

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.

Source