Реакция #56497

Уравнение реакции

hydrogen

hydrogen

hydrogen

4-{3-[3-[3-(1-Hydroxycyclohexyl)-2-propynyl]-4-oxo-2-thiazolidinyl]propyl}benzoic Acid

→

title product

4-{3-[3-[3-(1-Hydroxycyclohexyl)propyl]-4-oxo-2-thiazolidinyl]propyl}benzoic Acid

Растворители

ethyl acetate

Условия реакции

Обработка

1. 1
   workup.ADDITIONof catalyst is added
2. 2
   Другоеhas been absorbed
3. 3
   ДругоеThe catalyst is removed by filtration
4. 4
   Другоеthe solvent evaporated
5. 5
   ДругоеThe residual oil is chromatographed on silica gel with elution by 2% methanol in chloroform
6. 6
   ДругоеThe chromatographed product crystalizes when
7. 7
   Другоеtriturated with ether
8. 8
   ДругоеThere is obtained 1.2 g

Методика

4-{3-[3-[3-(1-Hydroxycyclohexyl)-2-propynyl]-4-oxo-2-thiazolidinyl]propyl}benzoic Acid (4.0 g., 0.01 mole) is dissolved in ethyl acetate (45 ml.) and hydrogenated at 25° C. and one atmosphere pressure over 1.0 g. of a 5% palladium on charcoal catalyst. When 0.01 mole of hydrogen is absorbed (2 hours), uptake of hydrogen becomes very slow. An additional 1.5 g. of catalyst is added and hydrogenation continued for 70 hours until 0.02 mole of hydrogen has been absorbed. The catalyst is removed by filtration and the solvent evaporated. The residual oil is chromatographed on silica gel with elution by 2% methanol in chloroform. The chromatographed product crystalizes when triturated with ether. There is obtained 1.2 g. of the title product, m.p. 118°-121° C.

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