Реакция #56496

Уравнение реакции

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

hydrogen

→

title product

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

Растворители

ethyl acetate

Условия реакции

Обработка

1. 1
   ДругоеThe catalyst is removed by filtration
2. 2
   Другоеthe solvent evaporated
3. 3
   ДругоеThe residual oil is chromatographed on 60 g
4. 4
   Промывкаof silica gel with elution by 2% methanol
5. 5
   ДругоеThe chromatographed product crystallizes
6. 6
   Другоеis recrystallized from butyl chloride
7. 7
   Другоеto yield 1.4 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 (50 ml.) and hydrogenated at 25° C. and one atmosphere pressure over 1.0 g. of a 5% palladium on charcoal catalyst. The theoretical amount (0.01 mole) of hydrogen is absorbed in 110 minutes. The catalyst is removed by filtration and the solvent evaporated. The residual oil is chromatographed on 60 g. of silica gel with elution by 2% methanol is chloroform. The chromatographed product crystallizes and is recrystallized from butyl chloride to yield 1.4 g. of the title product, m.p. 118°-120° C.; pmr (CDCl3) δ5.14 (1H, m, --CH2 --CH=), 5.60 (1H, d, ##STR46##

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