Allyl bromide → 3beta-Prop-2-enoxy-17beta(3-furyl)-5beta-androstan-14beta-ol

HRID 1647629Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1647629
[O:1]1[CH:5]=[CH:4][C:3]([C@H:6]2[CH2:11][CH2:10][C@:9]3([OH:26])[C@H:12]4[C@H:22]([CH2:23][CH2:24][C@:7]23[CH3:8])[C@:20]2([CH3:21])[C@@H:15]([CH2:16][C@@H:17]([OH:25])[CH2:18][CH2:19]2)[CH2:14][CH2:13]4)=[CH:2]1.[H-].[Na+].[CH2:29](Br)[CH:30]=[CH2:31]>O1CCCC1>[CH2:31]([O:25][C@H:17]1[CH2:18][CH2:19][C@@:20]2([CH3:21])[C@H:15]([CH2:14][CH2:13][C@@H:12]3[C@@H:22]2[CH2:23][CH2:24][C@@:7]2([CH3:8])[C@:9]3([OH:26])[CH2:10][CH2:11][C@@H:6]2[C:3]2[CH:4]=[CH:5][O:1][CH:2]=2)[CH2:16]1)[CH:30]=[CH2:29]

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 1606964617beta-(3-Furyl)-5beta,14beta-androstane-3beta,14beta-diol

Produkt 1

HCID 228545783beta-Prop-2-enoxy-17beta(3-furyl)-5beta-androstan-14beta-olAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 0.60 g of 17β-(3-furyl)-5β-androstane-3β,14β-diol (II-a: Ref. comp.) (Minato H. and Nagasaki T., J. Chem. Soc. (C), 1966, 377) in 50 ml of dry tetrahydrofuran, 0.44 g of sodium hydride (60% dispersion in mineral oil) were added under nitrogen atmosphere at room temperature and the resulting mixture was stirred at reflux temperature for 6 hrs; 1.4 g of allyl bromide were added and the reflux continued for further 20 hrs. The mixture was quenched with water and the organic solvent was distilled under reduced pressure. The residue was extracted with ethyl acetate, the organic solution was dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The residue was purified by flash-chromatography (SiO2) using n-hexane/ethyl acetate 80/20 as eluant to give 0.58 g of 3β-(prop-2-enoxy)-17β-(3-furyl)-5β-androstan-14β-ol as a white solid.

Aufarbeitung

  1. temperatureat reflux temperature for 6 hrs
  2. customThe mixture was quenched with water
  3. distillationthe organic solvent was distilled under reduced pressure
  4. extractionThe residue was extracted with ethyl acetate
  5. dry with materialthe organic solution was dried over anhydrous sodium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was purified by flash-chromatography (SiO2)

Quellen und Nachweise

ORD-Eintrag
ord-b97db43bf4314b74b6e07b894bd121ee
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05432169

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