Réaction #75217

ord-a0cb49e6e0d846a2ae9ba5022e8519d4

Équation de réaction

[H][H]
hydrogen
CCCCCCC#C[C@H]1CCC[C@@H]1SCCCCCC(=O)O
7-thia-13-prostynoic acid
→
CCCCCCCC[C@H]1CCC[C@@H]1SCCCCCC(=O)O
semisolid
Rendement 85.6%
CCCCCCCC[C@H]1CCC[C@@H]1SCCCCCC(=O)O
7-Thiaprostanoic Acid
Rendement 85.6%

Réactifs

[H][H]
hydrogen
CCCCCCC#C[C@H]1CCC[C@@H]1SCCCCCC(=O)O
7-thia-13-prostynoic acid

Réactifs

[Pd]
palladium on charcoal

Solvants

CCOC(C)=O
ethyl acetate
CCOC(C)=O
ethyl acetate

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreAfter 5 hrs the catalyst was removed by filtration
  2. 2
    Lavagewashed with ethyl acetate
  3. 3
    Autrethe combined filtrates evaporated

Mode opératoire

To a suspension of 50 mg of 10% palladium on charcoal in 1 ml of ethyl acetate, which had been pre-reduced with hydrogen gas was added 7-thia-13-prostynoic acid (15 mg) in 1.5 ml of ethyl acetate. After 5 hrs the catalyst was removed by filtration washed with ethyl acetate and the combined filtrates evaporated to yield 13 mg of a semisolid. Analysis by nmr indicated that there still remained starting material plus some 7-thia-13-cis-prostenoic acid. The material was therefore reduced again with 50 mg of fresh palladium catalyst for 1/2 hour and the reduced material isolated by filtration and removal of the solvent. 8 Milligrams of the saturated acid was obtained, which after recrystallization from hexane melted at 40°-41°.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04175201uspto-grants-1979_11