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

HRID 369699Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 369699
[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-4fd72dcb045b49c1ba7f61f564552f99
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06140316

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