9-Ethylenedioxy-15-keto-19-methyl-prost-13,18-dienoic acid, methyl ester → 9-Ethylenedioxy-15-keto-19-methyl-prost-18-enoic acid, methyl ester

HRID 27286Notes

Reaction equation

HRID 27286 reaction equation
[CH2:1]1[CH2:19][O:18][CH:17]2[CH:3]([C@@H:4]([C@@H:15]([CH:20]=[CH:21][C:22](=[O:29])[CH2:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])[CH2:16]2)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[O:2]1>C(OCC)(=O)C.[Pd]>[CH2:1]1[CH2:19][O:18][CH:17]2[CH:3]([C@@H:4]([C@@H:15]([CH2:20][CH2:21][C:22](=[O:29])[CH2:23][CH2:24][CH:25]=[C:26]([CH3:27])[CH3:28])[CH2:16]2)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[O:2]1

Participants

4

Reactant 1

HCID 867371899-Ethylenedioxy-15-keto-19-methyl-prost-13,18-dienoic acid, methyl ester

Product 1

HCID 867371889-Ethylenedioxy-15-keto-19-methyl-prost-18-enoic acid, methyl esterYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 3.6 g of 9-ethylenedioxy-15-keto-19-methyl-prost-13,18-dienoic acid, methyl ester, in ethyl acetate (100 ml.) 0.18 g of Pd/C (5%) are added and the mixture is hydrogenated at room temperature under pressure. After absorption of the theoretical quantity of hydrogen the catalyzer is separated by filtration and the solvent evaporated in vacuo to yield 3.4 g of 9-ethylenedioxy-15-keto-19-methyl-prost-18-enoic acid, methyl ester.

Workup

  1. customis hydrogenated at room temperature under pressure
  2. customAfter absorption of the theoretical quantity of hydrogen the catalyzer
  3. customis separated by filtration
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-7d907e6878924a7da34726ff2949ae5b
Source dataset
uspto-grants-1980_09
Patent number
US04220798

Reaction notes

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