Potassium Hydroxide → Colestolone

HRID 1199311Notes

Reaction equation

HRID 1199311 reaction equation
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

Participants

7

Reactant 4

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

Product 1

HCID 10046567Colestolone

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 10311-PropanolSolvent

Procedure

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).

Workup

  1. temperatureat reflux

Sources & evidence

ORD record
ord-b0d64963639d4b8d94295eb90ac1cb54
Source dataset
uspto-grants-1990_02
Patent number
US04900477

Reaction notes

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