Reaktion #926941

ord-800ea408627a4278b12efffdcf18ed77

Reaktionsgleichung

COc1cc2c(c(OC(C)=O)c1)[C@H]1CC[C@]3(C)C(=O)CC[C@H]3[C@@H]1CC2
1-acetoxy-3-methoxyestra-1,3,5(10)-trien-17-one
O
H2O
Cl
HCl
→
COc1cc(O)c2c(c1)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
1-hydroxy-3-methoxyestra-1,3,5(10)-trien-17-one

Edukte

COc1cc2c(c(OC(C)=O)c1)[C@H]1CC[C@]3(C)C(=O)CC[C@H]3[C@@H]1CC2
1-acetoxy-3-methoxyestra-1,3,5(10)-trien-17-one
O
H2O
Cl
HCl

Reagenzien

Keine

Lösungsmittel

[K+].[OH-]
potassium hydroxide

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeto give a white solid which
  2. 2
    Filtrationis filtered
  3. 3
    Sonstigerecrystallized from acetone-H2O

Vorschrift

A solution of 1-acetoxy-3-methoxyestra-1,3,5(10)-trien-17-one (7.0 g, 20.5 mM) in 150 ml of 5% anhydrous methanolic potassium hydroxide is stirred at room temperature for 1 hr. The resulting dark purple solution is added to 700 ml of cold H2O and acidified with 10% HCl to give a white solid which is filtered and recrystallized from acetone-H2O to give 1-hydroxy-3-methoxyestra-1,3,5(10)-trien-17-one, yield 5.4 g (88%), m.p. 220°-222°. Further recrystallization from ethyl acetate gives a product with a m.p. 226°-229°.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04096253uspto-grants-1978_06