Dihydrocholesterol → 3-Oxocholestane

HRID 842495

Reaktionsgleichung

Reaktionsgleichung von HRID 842495
[CH3:1][C@@H:2]([C@@H:9]1[C@@:13]2([CH3:28])[CH2:14][CH2:15][C@@H:16]3[C@@:21]4([CH3:27])[CH2:22][CH2:23][C@H:24]([OH:26])[CH2:25][C@@H:20]4[CH2:19][CH2:18][C@H:17]3[C@@H:12]2[CH2:11][CH2:10]1)[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7]>C(OCC)C.[Os](=O)(=O)(=O)=O>[CH3:8][CH:6]([CH2:5][CH2:4][CH2:3][C@H:2]([C@@H:9]1[C@:13]2([CH3:28])[C@H:12]([C@H:17]3[C@H:16]([CH2:15][CH2:14]2)[C@:21]2([CH3:27])[CH:20]([CH2:25][C:24](=[O:26])[CH2:23][CH2:22]2)[CH2:19][CH2:18]3)[CH2:11][CH2:10]1)[CH3:1])[CH3:7]

Komponenten

4

Edukt 1

HCID 6665Dihydrocholesterol

Produkt 1

HCID 108835733-OxocholestaneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

2.5 Millimole of 3β-cholestanol was dissolved in 50 ml of diethyl ether, and MCOsOx containing osmium tetroxide in an amount equivalent to 2.5 mmol was added thereto, followed by stirring at 25° C. for 30 hours to cause a reaction to take place. MCOsOx was removed from the reaction solution, and a crude keto compound was recovered from the filtrate and purified by silica gel column chromatography (eluent:benzene) to give 3-cholestanon at a yield of 90%.

Aufarbeitung

  1. additionwas added
  2. customa reaction
  3. customMCOsOx was removed from the reaction solution
  4. customa crude keto compound was recovered from the filtrate
  5. custompurified by silica gel column chromatography (eluent:benzene)

Quellen und Nachweise

ORD-Eintrag
ord-494ce304ac974530a2dfaf1a4fa9e2dd
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06376419B1

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