2-Mercaptoethanol → 2-(6-Carboxyhexyl)-4-(2-hydroxyethylthio)cyclopent-2-en-1-one

HRID 2083540Notes

Reaction equation

HRID 2083540 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:11](=[O:16])[CH2:12][CH:13](O)[CH:14]=1)([OH:3])=[O:2].[SH:17][CH2:18][CH2:19][OH:20].C[O-].[Na+]>CO>[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:11](=[O:16])[CH2:12][CH:13]([S:17][CH2:18][CH2:19][OH:20])[CH:14]=1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 3690897ACMC-20apjzHCID 10942334Sodium Methoxide

Product 1

HCID 233466542-(6-Carboxyhexyl)-4-(2-hydroxyethylthio)cyclopent-2-en-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In the manner of Example 281 a methanol solution of 2-(6-carboxyhexyl)-4-hydroxycyclopent-2-en-1-one [Prostaglandins, 3, 921 (1973)] and β-mercaptoethanol is treated with sodium methoxide solution, acidified, concentrated, and extracted to provide the subject compound as an oil.

Workup

  1. concentrationconcentrated
  2. extractionextracted

Sources & evidence

ORD record
ord-ecd6ae4c60504f6bbb8f82ea9bce7b82
Source dataset
uspto-grants-1978_04
Patent number
US04085272

Reaction notes

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