Reaktion #310629

ord-56fa0286287b4e47be76810483ecb679

Reaktionsgleichung

CCOCC
ether
COCCOCCl
β-methoxyethoxymethyl chloride
CCN(C(C)C)C(C)C
diisopropylethylamine
COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
Methyl lithocholate
→
COCCOCO[C@@H]1CC[C@@]2(C)[C@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)CCC=O)CC[C@@H]32)C1
3α-(β-methoxyethoxymethoxy)-5β-cholane-24-aldehyde

Edukte

CCOCC
ether
COCCOCCl
β-methoxyethoxymethyl chloride
CCN(C(C)C)C(C)C
diisopropylethylamine
COC(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
Methyl lithocholate

Reagenzien

Keine

Lösungsmittel

ClCCl
methylene chloride

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Waschenwashed with water
  2. 2
    SonstigeAfter drying the solvents
  3. 3
    Sonstigeare evaporated
  4. 4
    workup.DISSOLUTIONthe residue dissolved in toluene

Vorschrift

Methyl lithocholate is dissolved in methylene chloride, and β-methoxyethoxymethyl chloride and diisopropylethylamine are added. The mixture is stirred for four hours, ether added and washed with water. After drying the solvents are evaporated, the residue dissolved in toluene and the 24-ester group reduced to the 24-alcohol group with Vitride. The 24-alcohol then is oxidized with chromium trioxide-pyridine and the 3α-(β-methoxyethoxymethoxy)-5β-cholane-24-aldehyde obtained.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04354972uspto-grants-1982_10