Reaktion #1676322

ord-5e65a0fd213b492d9ee56f56cdfd4375

Reaktionsgleichung

C[C@]12CC[C@@H]3c4cccc(F)c4CC[C@H]3[C@@H]1CC[C@@H]2O
4-fluoroestra-1,3,5(10)-trien-17β-ol
→
C[C@]12CC[C@@H]3c4cccc(F)c4CC[C@H]3[C@@H]1CCC2=O
4-fluoroestra-1,3,5-(10)-trien-17-one

Edukte

C[C@]12CC[C@@H]3c4cccc(F)c4CC[C@H]3[C@@H]1CC[C@@H]2O
4-fluoroestra-1,3,5(10)-trien-17β-ol
—
ice water

Reagenzien

[Cr+6].[O-2].[O-2].[O-2]
chromium trioxide

Lösungsmittel

O=S(=O)(O)O
sulfuric acid
CC(C)=O
acetone

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe solids were collected
  2. 2
    workup.STIRRINGThe filter cake was stirred with methanol
  3. 3
    SonstigeThe inorganic salts were removed
  4. 4
    Sonstigethe filtrate was evaporated to dryness

Vorschrift

To a solution of 4-fluoroestra-1,3,5(10)-trien-17β-ol (100 mg, 0.36 mmol) in 1.5 ml of acetone at 0° C. was added, dropwise with stirring, a solution of 95 ml of 8N chromium trioxide in 8N sulfuric acid. After approximately 5 min. the reaction mixture was poured into 75 ml of ice water and the solids were collected. The filter cake was stirred with methanol. The inorganic salts were removed and the filtrate was evaporated to dryness to give the crude product, 4-fluoroestra-1,3,5-(10)-trien-17-one as a tan solid. The latter was crystallized from ether-petroleum ether (30°-60°) as a colorless solid (60 mg, 61% yield), mp 139°-141° C. Ir (KBr)cm-1 1724 (C17C=O), 1230 (aryl fluoride); 1H NMR δ 7.21-6.81 (m, 3, H1, H2, H3 aromatic) 2.91-1.54 (m, 15), 0.92 (s, 3, C18CH3).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04568673uspto-grants-1986_02