Reaktion #2144574

ord-e0077e78f91e4b4aa3016157807025f9

Reaktionsgleichung

CI
methyl iodide
[CH3][Mg][I]
methyl magnesium iodide
CCCCCC(=O)CS[C@H]1C(O)CC(O)[C@@H]1CC=CCCCC(=O)O
9,11-dihydroxy-15-oxo-13-thia-5-prostenoic acid
[Mg]
magnesium
→
CCCCCC(C)(O)CS[C@H]1C(O)CC(O)[C@@H]1CC=CCCCC(=O)O
9,11,15-trihydroxy-15-methyl-13-thia-5-prostenoic acid

Edukte

CI
methyl iodide
[CH3][Mg][I]
methyl magnesium iodide
CCCCCC(=O)CS[C@H]1C(O)CC(O)[C@@H]1CC=CCCCC(=O)O
9,11-dihydroxy-15-oxo-13-thia-5-prostenoic acid
[Mg]
magnesium

Reagenzien

Keine

Lösungsmittel

CCOCC
diethyl ether
CCOCC
diethyl ether

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONAdd dropwise 0.37 g
  2. 2
    Sonstigethe reaction for one hour
  3. 3
    workup.ADDITIONpour into 50 ml
  4. 4
    Extraktionsaturated aqueous NH4Cl solution, extract with diethyl ether
  5. 5
    Trocknendry the organic phase over Na2SO4
  6. 6
    workup.DISTILLATIONdistill off the solvent

Vorschrift

Add dropwise 0.37 g. 9,11-dihydroxy-15-oxo-13-thia-5-prostenoic acid, dissolved in 10 ml. dry diethyl ether, to a methyl magnesium iodide solution, prepared from 0.024 g. magnesium shavings and 0.14 g. methyl iodide in 15 ml. dry diethyl ether, stir the reaction for one hour, pour into 50 ml. saturated aqueous NH4Cl solution, extract with diethyl ether, dry the organic phase over Na2SO4 and distill off the solvent to obtain, as the residue, 9,11,15-trihydroxy-15-methyl-13-thia-5-prostenoic acid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04210651uspto-grants-1980_07