7-Thia-13-prostynoic acid → 7-Thiaprostanoic Acid

HRID 46939Notes

Reaction equation

HRID 46939 reaction equation
[H][H].[C:3]([OH:24])(=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9][C@@H:10]1[C@@H:14]([C:15]#[C:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:13][CH2:12][CH2:11]1>[Pd].C(OCC)(=O)C>[C:3]([OH:24])(=[O:23])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9][C@@H:10]1[C@@H:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 227970457-Thia-13-prostynoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 227970467-Thiaprostanoic AcidYield 85.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

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°.

Workup

  1. customAfter 5 hrs the catalyst was removed by filtration
  2. washwashed with ethyl acetate
  3. customthe combined filtrates evaporated

Sources & evidence

ORD record
ord-a0cb49e6e0d846a2ae9ba5022e8519d4
Source dataset
uspto-grants-1979_11
Patent number
US04175201

Reaction notes

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