Pyridinium → HCID 86748908, Verbindung

HRID 1735742Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1735742
[NH+]1C=CC=CC=1.[OH:7][C@H:8]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C@H:10]([CH2:11][CH2:12][C@@H:13]3[C@@H:22]2[CH2:21][CH2:20][C@@:18]2([CH3:19])[C@:14]3([OH:29])[CH2:15][CH2:16][C@@H:17]2[CH:27]=[O:28])[CH2:9]1>ClCCl.C(OCC)C>[O:7]=[C:8]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C@H:10]([CH2:11][CH2:12][C@@H:13]3[C@@H:22]2[CH2:21][CH2:20][C@@:18]2([CH3:19])[C@:14]3([OH:29])[CH2:15][CH2:16][C@@H:17]2[CH:27]=[O:28])[CH2:9]1

Komponenten

5

Edukt 2

HCID 4989215PyridiniumHCID 109033043beta,14beta-Dihydroxy-5beta-androstane-17beta-carboxaldehyde

Produkt 1

HCID 86748908HCID 86748908, VerbindungAusbeute 60,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a suspension of 0.88 g of pyridinium dicromate in 2.2 ml of dichloromethane a solution of 0.50 g of 3β,14β-dihydroxy-5β-androstane-17β-carboxaldehyde (Boutagy J. and Thomas R., Aust. J. Chem., 1971, 24, 2723) in 2.5 ml of dichloromethane was added at room temperature. After 20 hrs the mixture was diluted with diethyl ether and filtered through celite; the filtrate was evaporated to dryness under reduced pressure. The crude product was purified by flash-chromatography (SiO2) using n-hexane/ethyl acetate 6/4 as eluant; the fractions containing the title compound were collected and evaporated to give 0.30 g of the title compound (II-e) as a white foam.

Aufarbeitung

  1. additionwas added at room temperature
  2. filtrationfiltered through celite
  3. customthe filtrate was evaporated to dryness under reduced pressure
  4. customThe crude product was purified by flash-chromatography (SiO2)
  5. additionthe fractions containing the title compound
  6. customwere collected
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-480f0e896c874bd8aec6782c4f7528c3
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05538960

Notizen zur Reaktion

Wird geladen…