Sodium Hydroxide → 9-Keto-15-hydroxy-19-methyl-prosta-13,18-dienoic acid

HRID 27288Notes

Reaction equation

HRID 27288 reaction equation
[O:1]=[C:2]1[CH2:16][CH2:15][C@H:14]([CH:17]=[CH:18][CH:19]([OH:26])[CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[C@H:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12]C)=[O:11].[OH-].[Na+]>O.CO>[O:1]=[C:2]1[CH2:16][CH2:15][C@H:14]([CH:17]=[CH:18][CH:19]([OH:26])[CH2:20][CH2:21][CH:22]=[C:23]([CH3:24])[CH3:25])[C@H:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 705889469-Keto-15-hydroxy-19-methyl-prosta-13,18-dienoic acid, methyl ester

Product 1

HCID 705893249-Keto-15-hydroxy-19-methyl-prosta-13,18-dienoic acidYield 91.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

The solution of 0.5 g of 9-keto-15-hydroxy-19-methyl-prosta-13,18-dienoic acid, methyl ester, 0.170 g of NaOH in water (1.5 ml), methanol (4.5 ml) is left for two hours at room temperature under nitrogen, then diluted with water (22 ml) and extracted with diethyl ether (10 ml). The aqueous layer is acidified (congo red) with HCl (5%), then extracted with diethyl ether (3×15 ml). The ethereal solution is washed with water to neutrality, dried over sodium sulphate and the solvent evaporated in vacuo to yield 0.44 g of 9-keto-15-hydroxy-19-methyl-prosta-13,18-dienoic acid (oil).

Workup

  1. extractionextracted with diethyl ether (10 ml)
  2. extractionextracted with diethyl ether (3×15 ml)
  3. washThe ethereal solution is washed with water to neutrality
  4. dry with materialdried over sodium sulphate
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-5aade86bc8c34ac1a1e755e1dd61b1eb
Source dataset
uspto-grants-1980_09
Patent number
US04220798

Reaction notes

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