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Methyl iodide → 16alpha-Fluoro-1beta,6beta-dimethyl-7-methylenandrost-4-ene-3,17-dione

HRID 621621
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 621621
C1CO[CH:20]2[CH:3]([CH2:4][C:5]34O[C@H:6]3[C:7](=[CH2:30])[C@@H:8]3[C@@H:17]([C@@:18]4([CH3:24])[C@@H:19]2[CH3:23])[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][C@:11]3([F:29])OCC[O:25][CH:12]32)[O:2]1.[Mg].[CH3:33]I>C1C=CC=CC=1.C(OCC)C>[F:29][C@@H:11]1[CH2:10][C@H:9]2[C@H:8]3[C@H:17]([CH2:16][CH2:15][C@:13]2([CH3:14])[C:12]1=[O:25])[C@:18]1([CH3:24])[C:5](=[CH:4][C:3](=[O:2])[CH2:20][C@H:19]1[CH3:23])[C@H:6]([CH3:33])[C:7]3=[CH2:30]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 5462224MagnesiumHCID 867429553,17-Bis(ethylenedioxy)-5,6alpha-epoxy-16alpha-fluoro-1beta-methyl-7-methylenandrostane

Produkt 1

HCID 1863203316alpha-Fluoro-1beta,6beta-dimethyl-7-methylenandrost-4-ene-3,17-dioneAusbeute 80,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241
Benzene
Lösungsmittel
HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

3,17-bis(ethylenedioxy)-5,6α-epoxy-16α-fluoro-1β-methyl-7-methylenandrostane (431 mg) in benzene solution (40 ml), is added to a Grignard mixture prepared from magnesium (122 mg) and methyl iodide (710 mg) in diethylether (10 ml). Solvent is removed until the boiling point reaches ~78° C. Heating is then continued for a further 3 hrs. Ice and saturated ammonium chloride solution are added, the product extracted with ethyl acetate and the organic layer is evaporated in vacuo after having washed and dried it. The residue is dissolved in a 2:1 mixture of acetic acid and water (10 ml) and the solution heated for about 6 hrs at 40°-50° C. Then water is added and the product extracted with ethyl acetate. The organic layer is washed with sodium bicarbonate solution, dried and evaporated in vacuo. The residue is submitted to column chromatography thus giving pure 16α-fluoro-1β,6β-dimethyl-7-methylenandrost-4-ene-3,17-dione (275 mg).

Aufarbeitung

  1. customSolvent is removed until the boiling point
  2. customreaches ~78° C
  3. temperatureHeating
  4. additionIce and saturated ammonium chloride solution are added
  5. extractionthe product extracted with ethyl acetate
  6. customthe organic layer is evaporated in vacuo
  7. washafter having washed
  8. customdried it
  9. dissolutionThe residue is dissolved in a 2:1 mixture of acetic acid and water (10 ml)
  10. temperaturethe solution heated for about 6 hrs at 40°-50° C
  11. additionThen water is added
  12. extractionthe product extracted with ethyl acetate
  13. washThe organic layer is washed with sodium bicarbonate solution
  14. customdried
  15. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b6736ce1a3d04ad681e652de49cdcafb
Quelldatensatz
uspto-grants-1989_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04824830

Notizen zur Reaktion

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