반응 #56496

반응 방정식

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

용매

ethyl acetate

반응 조건

후처리

1. 1
   기타The catalyst is removed by filtration
2. 2
   기타the solvent evaporated
3. 3
   기타The residual oil is chromatographed on 60 g
4. 4
   세척of silica gel with elution by 2% methanol
5. 5
   기타The chromatographed product crystallizes
6. 6
   기타is recrystallized from butyl chloride
7. 7
   기타to yield 1.4 g

실험 절차

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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