Reaktion #81727

ord-20dec9601cad4b28adb26edc2aa51fff

Reaktionsgleichung

COC(=O)c1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](C(=O)C3CCCCC3)CC[C@@H]12
methyl-17β-cyclohexylcarbonyl-estra-1,3,5(10)-triene-3-carboxylate
O=C([O-])[O-].[K+].[K+]
K2CO3
O
water
CO
methanol
→
C[C@]12CC[C@@H]3c4ccc(C(=O)O)cc4CC[C@H]3[C@@H]1CC[C@@H]2C(=O)C1CCCCC1
title compound
C[C@]12CC[C@@H]3c4ccc(C(=O)O)cc4CC[C@H]3[C@@H]1CC[C@@H]2C(=O)C1CCCCC1
17β-Cyclohexylcarbonyl-estra-1,3,5(10)-triene-3-carboxylic Acid

Edukte

COC(=O)c1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](C(=O)C3CCCCC3)CC[C@@H]12
methyl-17β-cyclohexylcarbonyl-estra-1,3,5(10)-triene-3-carboxylate
O=C([O-])[O-].[K+].[K+]
K2CO3
O
water
CO
methanol

Reagenzien

Keine

Lösungsmittel

CCOC(C)=O
ethyl acetate

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturwas heated
  2. 2
    Temperaturat reflux overnight
  3. 3
    EinengenThe reaction mixture was then concentrated
  4. 4
    workup.ADDITIONThe residue was diluted with water
  5. 5
    Extraktionextracted with ethyl acetate
  6. 6
    ExtraktionThe organic extract
  7. 7
    Waschenwas washed with brine
  8. 8
    Sonstigedried
  9. 9
    Einengenconcentrated
  10. 10
    WaschenThe resulting solid was washed with CH3CN
  11. 11
    Sonstigeisolated by filtration
  12. 12
    Sonstigeto give

Vorschrift

A mixture of methyl-17β-cyclohexylcarbonyl-estra-1,3,5(10)-triene-3-carboxylate (0.14 g, 0.34 mmol), K2CO3 (0.2 g, 1.45 mmol), water (3.0 mL) and methanol (30 mL) was heated at reflux overnight. The reaction mixture was then concentrated. The residue was diluted with water, acidified with dilute HCl and extracted with ethyl acetate. The organic extract was washed with brine, dried, and concentrated. The resulting solid was washed with CH3CN and isolated by filtration from boiling ethyl acetate to give, 0. 11 g of the title compound. mp 280°-285° C. (softened at 260° C.).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05618806uspto-grants-1997_04