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 27285Notes

Reaction equation

HRID 27285 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(O)C.[Ni]>[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 88.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To the solution of 4.4 g of 9-ethylenedioxy-15-keto-19-methyl-prost-13,18-dienoic acid, methyl ester, in ethanol (60 ml.) are added 0.8 g of Raney-nickel washed with ethanol 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 3.9 g of 9-ethylenedioxy-15-keto-19-methyl-prost-18-enoic acid, methyl ester.

Workup

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

Sources & evidence

ORD record
ord-52ae009c01cd4b96bb9603d8a5883f79
Source dataset
uspto-grants-1980_09
Patent number
US04220798

Reaction notes

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