Sodium Fluoride → 3beta-Acetoxy-5alpha,6beta-dichloro-14alpha-fluoropregnan-20-one

HRID 894507

Reaktionsgleichung

Reaktionsgleichung von HRID 894507
[C:1]([O:4][C@H:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@:7]([Cl:28])([C@H:8]([Cl:27])[CH2:9][C@@H:10]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1)(=[O:3])[CH3:2].[F:29]C(F)(F)C([O-])=O.[Na+].[F-].[Na+].FF>FC(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[C:1]([O:4][C@H:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@:7]([Cl:28])([C@H:8]([Cl:27])[CH2:9][C@@H:10]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@@:11]3([F:29])[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1)(=[O:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 5235Sodium FluorideHCID 24524Fluorine2×HCID 517019Sodium TrifluoroacetateHCID 705691213beta-Acetoxy-5alpha,6beta-dichloropregnan-20-one

Produkt 1

HCID 705694493beta-Acetoxy-5alpha,6beta-dichloro-14alpha-fluoropregnan-20-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 6389TrichlorofluoromethaneLösungsmittel

Versuchsvorschrift

3β-Acetoxy-5α,6β-dichloropregnan-20-one (1.4 g) was dissolved in fluorotrichloromethane (250 ml) and chloroform (200 ml) containing sodium trifluoroacetate (ca. 2 g) and sodium fluoride (ca. 2 g). The resulting solution was cooled to -78° and vigourously stirred, whereupon fluorine from four 750 cc bottles (10% v/v fluorine in nitrogen) was bubbled through the solution over a period of 8 hours. The reaction solution was then poured into aqueous sodium thiosulphate and the organic layer was separated, washed with water, dried over potassium carbonate and evaporated to dryness to yield crude 3β-acetoxy-5α,6β-dichloro-14α-fluoropregnan-20-one.

Aufarbeitung

  1. temperatureThe resulting solution was cooled to -78°
  2. customwas bubbled through the solution over a period of 8 hours
  3. additionThe reaction solution was then poured into aqueous sodium thiosulphate
  4. customthe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over potassium carbonate
  7. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-234168b7e3f6491997a2f83d137b1c78
Quelldatensatz
uspto-grants-1981_08
Patentnummer
US04284558

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