반응 #2382243

반응 방정식

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

→

Compound B

수율 7.2%

5-{[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene}-4-thiazolidinone

수율 7.2%

용매

ethanol

반응 조건

후처리

1. 1
   여과The reaction mixture was filtered
2. 2
   기타evaporated to dryness
3. 3
   workup.DISSOLUTIONIn sections, the material was dissolved in 1 volume of hot ethyl acetate
4. 4
   workup.ADDITIONdiluted with 2 volumes of hexane
5. 5
   여과filtered
6. 6
   세척Elution with 35% ethyl acetate in hexane provided various fractions which

실험 절차

A solution of 69.90 g of 5-{[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene}-2-thioxo-4-thiazolidinone in 4 liters of ethanol was hydrogenated at 500 pounds per square inch (psi) in the presence of 200 g of 5% palladium on carbon overnight at 100° C. The reaction mixture was filtered and evaporated to dryness. In sections, the material was dissolved in 1 volume of hot ethyl acetate, diluted with 2 volumes of hexane, filtered, and loaded onto a silica gel chromatography column. Elution with 35% ethyl acetate in hexane provided various fractions which were combined according to the purities of the respective compounds. A total of 4.6 g of Compound B were isolated by chromatography. Fractions which were predominantly Compound B were crystallized from ethyl acetate/hexane providing a total yield of Compound B of 13.79 g. Rechromatography of fractions containing impure Compound C on silica eluting with 25% ethyl acetate in hexane provided 9.82 g of Compound C.

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