Sodium sulfate decahydrate → Estra-4,16-dien-3-ol

HRID 275673Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 275673
[CH3:1][C@:2]12[CH2:18][CH2:17][C@H:16]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@@H:15]3[CH2:14][CH2:13][C:12](=[O:19])[CH:11]=4)[C@@H:6]1[CH2:5][CH:4]=[CH:3]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>CCOCC>[CH3:1][C@:2]12[CH2:18][CH2:17][C@H:16]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@@H:15]3[CH2:14][CH2:13][CH:12]([OH:19])[CH:11]=4)[C@@H:6]1[CH2:5][CH:4]=[CH:3]2

Komponenten

5

Edukt 3

HCID 62649Sodium sulfate decahydrateHCID 15870982Estra-4,16-dien-3-one2×HCID 21226445Aluminium lithium hydride

Produkt 1

HCID 54095959Estra-4,16-dien-3-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To estra-4,16-dien-3-one, (1) (87.2 mg, 0.340 mmol) in 1.7 mL of anh. ether was added. lithium aluminum hydride (15.0 mg, 0.395 mmol) and the suspension was stirred 17 min. Reaction was then agitated 10 min. with 0.50 g of sodium sulfate decahydrate and filtered through Celite. The residue was washed with three 10 mL portions of ether and the combined filtrates were concentrated under reduced pressure. Preparative TLC (5% ethyl acetate/dichloro-methane on silica gel) gave crude product (50.0 mg) as a yellow resin. This could be rechromatographed until sufficiently pure.

Aufarbeitung

  1. customReaction
  2. filtrationfiltered through Celite
  3. washThe residue was washed with three 10 mL portions of ether
  4. concentrationthe combined filtrates were concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8f1da857e57c4afdad795a0342a56d27
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06352980B1

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