Reacción #3034

Ecuación de reacción

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

diethyl 2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate

ethyl acetate

→

desired title product

Rendimiento 56.9%

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

Rendimiento 56.9%

Disolventes

toluene

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroForty grams of silica gel 60 (finer than 230 mesh) previously dried in vacuo at 50° C. for 7 hours
2. 2
   workup.ADDITIONwere added to the reaction
3. 3
   TemperaturaThe reaction was heated
4. 4
   Temperaturaat reflux for 18 hours
5. 5
   Filtraciónfiltered hot
6. 6
   OtroThe filtrate was evaporated to dryness
7. 7
   workup.DISSOLUTIONThe residue was dissolved in 500 ml of ethyl acetate
8. 8
   Lavadowashed 5 times each with 400 ml of 1N hydrochloric acid
9. 9
   Secadodried over sodium sulfate
10. 10
    Filtraciónfiltered
11. 11
    Otroevaporated in vacuo
12. 12
    Otroto provide a yellow solid

Procedimiento

Under a nitrogen atmosphere, 13.98 g of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-thioxo-4-thiazolidinone, 13.17 g of diethyl 2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate and 600 ml of toluene were stirred to effect solution. Forty grams of silica gel 60 (finer than 230 mesh) previously dried in vacuo at 50° C. for 7 hours were added to the reaction. The reaction was heated at reflux for 18 hours and filtered hot. The filtrate was evaporated to dryness. The residue was dissolved in 500 ml of ethyl acetate, washed 5 times each with 400 ml of 1N hydrochloric acid, dried over sodium sulfate, filtered, and evaporated in vacuo to provide a yellow solid. Chromatography over silica gel eluting with 2.5% ethyl acetate in toluene provided 8.0 g of the desired title product, m.p. 178°-179° C.

Fuente