Reaktion #1243232

ord-520c637ca4c04b8495259d59827aea9b

Reaktionsgleichung

CC[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CCC4=C3C=C[C@]2(C)[C@H]1OC(C)=O
17β-acetoxy-16α-ethyl-4,9,11-estratrien-3-one
O=C([O-])[O-].[K+].[K+]
potassium carbonate
→
CC[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CCC4=C3C=C[C@]2(C)[C@H]1O
16α-ethyl-17β-hydroxy-4,9,11-estratrien-3-one
Ausbeute 86.7%

Edukte

CC[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CCC4=C3C=C[C@]2(C)[C@H]1OC(C)=O
17β-acetoxy-16α-ethyl-4,9,11-estratrien-3-one
O=C([O-])[O-].[K+].[K+]
potassium carbonate

Reagenzien

Keine

Lösungsmittel

CO
methanol
O
water
O
water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktionextracted with ethyl acetate
  2. 2
    SonstigeCrystallization of the crude product from ethyl acetate

Vorschrift

A solution of 2.5 g of 17β-acetoxy-16α-ethyl-4,9,11-estratrien-3-one in 120 ml of methanol and 5 ml of water is stirred, after adding 6.0 g of potassium carbonate, for 4 hours at room temperature. The mixture is then poured into water and extracted with ethyl acetate. Crystallization of the crude product from ethyl acetate yields 1.9 g of 16α-ethyl-17β-hydroxy-4,9,11-estratrien-3-one, m.p. 139°-141° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04333928uspto-grants-1982_06