Diethyl Ether → HCID 22821826, compound

HRID 223447Notes

Reaction equation

HRID 223447 reaction equation
[CH3:1][C@@H:2]([C@@H:9]1[C@@:13]2([CH3:28])[CH2:14][CH2:15][C@@H:16]3[C@@:21]4([CH3:27])[CH2:22][CH2:23][C@@H:24]([OH:26])[CH2:25][C@H:20]4[CH2:19][CH2:18][C@H:17]3[C@@H:12]2[CH2:11][CH2:10]1)[CH2:3][CH2:4][C:5](OC)=[O:6].[CH3:29][O:30][CH2:31][CH2:32][O:33][CH2:34]Cl.C(N(C(C)C)CC)(C)C.CCOCC>C(Cl)Cl>[CH3:29][O:30][CH2:31][CH2:32][O:33][CH2:34][O:26][C@@H:24]1[CH2:23][CH2:22][C@@:21]2([CH3:27])[C@H:20]([CH2:19][CH2:18][C@@H:17]3[C@@H:16]2[CH2:15][CH2:14][C@@:13]2([CH3:28])[C@H:12]3[CH2:11][CH2:10][C@@H:9]2[C@H:2]([CH3:1])[CH2:3][CH2:4][CH:5]=[O:6])[CH2:25]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531DiisopropylethylamineHCID 92880Methyl lithocholate

Product 1

HCID 22821826HCID 22821826, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. washwashed with water
  2. customAfter drying the solvents
  3. customare evaporated
  4. dissolutionthe residue dissolved in toluene

Sources & evidence

ORD record
ord-56fa0286287b4e47be76810483ecb679
Source dataset
uspto-grants-1982_10
Patent number
US04354972

Reaction notes

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