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Imidazole → HCID 14800132, Verbindung

HRID 1885796
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1885796
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:17]([CH2:18][CH2:19][C@:3]12[CH3:4])[C@@H:16]1[C@H:11]([CH2:12][C:13](=[O:20])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.N1C=CN=C1.[C:26]([Si:30](Cl)([CH3:32])[CH3:31])([CH3:29])([CH3:28])[CH3:27].CCCCCC.CCOC(C)=O>CN(C=O)C.O>[Si:30]([O:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:17]([CH2:18][CH2:19][C@:3]12[CH3:4])[C@@H:16]1[C@H:11]([CH2:12][C:13](=[O:20])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:32])[CH3:31]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 9420217beta-Hydroxy-5alpha-estran-3-oneHCID 21226206Ethyl acetate hexane

Produkt 1

HCID 14800132HCID 14800132, VerbindungAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

10 g of 17β-hydroxy-5α-estran-3-one was dissolved in 150 ml of DMF. 3.7 g of imidazole were then added and the mixture was cooled to 0° C. 6.5 g of t-butyl dimethyl silyl chloride were added and the mixture was stirred and gradually warmed to room temperature followed by stirring for two days. TLC (hexane/EtOAc (9:1)) revealed that the reaction was complete. The reaction mixture was diluted with water and then extracted with 500 ml of hexane/EtOAc (9:1) (2×). The combined organic layers were washed with brine, dried over MgSO4, filtered, and evaporated under reduced pressure to produce crude product (14.6 g). The entire crude yield was flash chromatographed with the Aldrich flash chromatography system. The 600 ml column was filled with 7 inches of 230-400 mesh silica gel, eluting with hexane/EtOAc (10:1). Once the sample was loaded, 30 ml fractions were taken. Fraction numbers 4-13 yielded 14 g of the title compound, m.p. 103°-104° C.

Aufarbeitung

  1. temperaturegradually warmed to room temperature
  2. stirringby stirring for two days
  3. extractionextracted with 500 ml of hexane/EtOAc (9:1) (2×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customto produce crude product (14.6 g)
  9. customThe entire crude yield
  10. customchromatographed with the Aldrich flash chromatography system
  11. additionThe 600 ml column was filled with 7 inches of 230-400 mesh silica gel
  12. washeluting with hexane/EtOAc (10:1)

Quellen und Nachweise

ORD-Eintrag
ord-54f126410e20477999ae51cf37d3d620
Quelldatensatz
uspto-grants-1992_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05145874

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