Reaktion #1446055

ord-25f1508461fe4c6daf5b4946f662357a

Reaktionsgleichung

[I-].[Na+]
sodium iodide
C[C@]12C[C@H](c3ccc(OCCCCCCCl)cc3)[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CC[C@@H]2O
product
C[C@]12C[C@H](c3ccc(OCCCCCCCl)cc3)[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CC[C@@H]2O
11beta-[4-[(6-chloro hexyl)oxy]phenyl]estra-1,3,5(10)-triene-3,17beta-diol
[I-].[Na+]
sodium iodide
→
C[C@]12C[C@H](c3ccc(OCCCCCCI)cc3)[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CC[C@@H]2O
11beta-[4-[(6-iodo hexyl)oxy]phenyl]estra-1,3,5(10)-triene-3,17beta-diol

Edukte

[I-].[Na+]
sodium iodide
C[C@]12C[C@H](c3ccc(OCCCCCCCl)cc3)[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CC[C@@H]2O
product
C[C@]12C[C@H](c3ccc(OCCCCCCCl)cc3)[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CC[C@@H]2O
11beta-[4-[(6-chloro hexyl)oxy]phenyl]estra-1,3,5(10)-triene-3,17beta-diol
[I-].[Na+]
sodium iodide

Reagenzien

Keine

Lösungsmittel

CCC(C)=O
methylethylketone
CCOC(C)=O
ethyl acetate

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturunder reflux
  2. 2
    workup.WAITfollowed by agitation for 2 hours
  3. 3
    Temperaturunder reflux and for 16 hours
  4. 4
    Sonstigewhile leaving the temperature
  5. 5
    Waschenwashing
  6. 6
    Sonstigedrying
  7. 7
    Sonstigeevaporating to dryness under reduced pressure
  8. 8
    Sonstige470 mg of expected product is collected which

Vorschrift

150 mg of sodium iodide is added to a solution of 310 mg of the product obtained in Stage C in 6 cm3 of methylethylketone and agitation is carried out for 24 hours under reflux. 100 mg of sodium iodide is added, followed by agitation for 2 hours under reflux and for 16 hours while leaving the temperature to return to ambient, taking up in ethyl acetate, washing, drying and evaporating to dryness under reduced pressure. 470 mg of expected product is collected which is used as it is for the following stage.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06596885B2uspto-grants-2003_07