Reaktion #926940

ord-4fa104b4f9f845d68230a826d14986e6

Reaktionsgleichung

CC(=O)Oc1cc(O)cc2c1[C@H]1CC[C@]3(C)C(=O)CC[C@H]3[C@@H]1CC2
1-Acetoxy-3-hydroxyestra-1,3,5(10)-trien-17-one
CC(C)=O
acetone
→
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

Edukte

CC(=O)Oc1cc(O)cc2c1[C@H]1CC[C@]3(C)C(=O)CC[C@H]3[C@@H]1CC2
1-Acetoxy-3-hydroxyestra-1,3,5(10)-trien-17-one
CC(C)=O
acetone

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeequipped with condenser, magnetic stirring bar
  2. 2
    Sonstigedrying tube and pressure-compensated addition funnel
  3. 3
    workup.ADDITIONDimethyl sulfate (3.2 g, 25 mM) is added
  4. 4
    Temperaturthe resulting suspension is refluxed for 16 hrs
  5. 5
    Filtrationfiltered
  6. 6
    Temperaturwhile still warm
  7. 7
    WaschenThe filter cake is washed repeatedly with anhydrous acetone
  8. 8
    Sonstigethe combined filtrates are evaporated in vacuo
  9. 9
    SonstigeThe residue is recrystallized from acetone-water

Vorschrift

1-Acetoxy-3-hydroxyestra-1,3,5(10)-trien-17-one (7.6 g, 23 mM) is added to 600 ml of anhydrous acetone in a 3-neck, 1 liter round bottom flask equipped with condenser, magnetic stirring bar, drying tube and pressure-compensated addition funnel. Dimethyl sulfate (3.2 g, 25 mM) is added and the resulting suspension is refluxed for 16 hrs, and then filtered while still warm. The filter cake is washed repeatedly with anhydrous acetone, and the combined filtrates are evaporated in vacuo. The residue is recrystallized from acetone-water to obtain 1-acetoxy-3-methoxyestra-1,3,5(10)-trien-17-one, yield 6.2 g (80%), m.p. 144°-145°. Further recrystallization from CH2Cl2 -hexane gives material of m.p. 150°-151°.

Quelle

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