Potassium Hydroxide → Colestolone

HRID 1199311Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1199311
C([O:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:12]([CH2:13][CH2:14][C:15]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C:16]=3[C:17](=[O:37])[CH2:18][C@@H:19]2[C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:11]1)(=O)C1C=CC=CC=1.Cl(O)(=O)(=O)=O.[OH-].[K+].CO.[OH-].[Na+]>C(O)CC.C(O)C>[OH:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:12]([CH2:13][CH2:14][C:15]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C:16]=3[C:17](=[O:37])[CH2:18][C@@H:19]2[C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:11]1

Komponenten

7

Edukt 4

HCID 14797Potassium HydroxideHCID 24247Perchloric AcidHCID 11249146HCID 11249146, VerbindungHCID 23721981Sodium hydroxide methanol

Produkt 1

HCID 10046567Colestolone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 10311-PropanolLösungsmittel

Versuchsvorschrift

Then a stirred mixture of the precursor (6) in a protic solvent, preferably methanol, is treated with potassium carbonate and heated at reflux for 3 hours to give the desired product (3β,5α)-3-hydroxycholest-8(14)en-15-one (7). This conversion was based upon the procedures of E. J. Parish and G. J. Schroepfer and J. Org. Chem., 45, 4034-4037 (1980) and R. E. Dolle and L. Kruse, J. Org. Chem., 51, 4047-4053 (1986). Alternatively, the precursor (6) is treated with perchloric acid in n-propanol or ethanol at reflux or treated with potassium hydroxide or sodium hydroxide methanol at room temperature to give the desired product (7).

Aufarbeitung

  1. temperatureat reflux

Quellen und Nachweise

ORD-Eintrag
ord-b0d64963639d4b8d94295eb90ac1cb54
Quelldatensatz
uspto-grants-1990_02
Patentnummer
US04900477

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