Ethyl Acetate → 5α-Cholest-8(14)-en-3β-ol

HRID 1490393Notes

Reaction equation

HRID 1490393 reaction equation
[CH2:1]=[C:2]([CH:4]=[CH:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[CH:16]([CH2:17][CH2:18][CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[H][H].C(OCC)(=[O:32])C>C(O)(=O)C.[Pt]=O>[CH3:8][C@@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C:12](=[C:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C@H:16]([CH2:17][C@@H:18]([OH:32])[CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[CH2:6][CH2:5][CH2:4][CH:2]([CH3:3])[CH3:1]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 71401261HCID 71401261, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 52836655α-Cholest-8(14)-en-3β-olYield 99%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

50 g of cholestadiene (98%, Aldrich GmbH, Steinheim) are dissolved in 800 ml of dry ethyl acetate to which 30 ml of acetic acid have been added, 1.5 g of platinum oxide are added, and the mixture is transferred into an autoclave with a capacity of 2 l. The hydrogenation is carried out at 50° C. and a hydrogen pressure of 10 atm and is generally complete after 24 hours. When the reaction is complete, the catalyst is filtered off, the solvent is removed on a rotary evaporator, and the doristerol obtained is recrystallized from ethanol. Yield: 42.5 g (88.5%). The purity of the substance is ensured with the aid of 1H-NMR and 13C-NMR spectroscopy.

Workup

  1. additionhave been added
  2. customis carried out at 50° C.
  3. filtrationthe catalyst is filtered off
  4. customthe solvent is removed on a rotary evaporator

Sources & evidence

ORD record
ord-3819a5cb0ebf4b4ba8577abeae59a4a3
Source dataset
uspto-grants-1997_10
Patent number
US05682212

Reaction notes

Loading…