Reaction #310629

ord-56fa0286287b4e47be76810483ecb679

Reaction equation

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

Reactants

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

Reagents

None

Solvents

ClCCl
methylene chloride

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Washwashed with water
  2. 2
    OtherAfter drying the solvents
  3. 3
    Otherare evaporated
  4. 4
    workup.DISSOLUTIONthe residue dissolved in toluene

Procedure

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.

Source

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