Ethylene Glycol → 24-Ethylenedioxycholesterol

HRID 1578248Notes

Reaction equation

HRID 1578248 reaction equation
[O:1]=[C:2]([CH2:6][CH2:7][C@H:8]([C@@H:10]1[C@:28]2([CH3:29])[C@H:13]([C@H:14]3[C@H:25]([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C:17]([CH2:18][C@H:19]([CH2:21][CH2:22]2)[OH:20])=[CH:16][CH2:15]3)[CH2:12][CH2:11]1)[CH3:9])[CH:3]([CH3:5])[CH3:4].[CH2:30](O)[CH2:31][OH:32].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH2:30]1[CH2:31][O:32][CH:6]([CH2:7][C@H:8]([C@@H:10]2[C@:28]3([CH3:29])[C@H:13]([C@H:14]4[C@H:25]([CH2:26][CH2:27]3)[C@:23]3([CH3:24])[C:17]([CH2:18][C@H:19]([CH2:21][CH2:22]3)[OH:20])=[CH:16][CH2:15]4)[CH2:12][CH2:11]2)[CH3:9])[CH:2]([CH:3]([CH3:5])[CH3:4])[O:1]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962Water2×HCID 6101p-Toluenesulfonic acidHCID 1103680824-Ketocholesterol

Product 1

HCID 7052190124-Ethylenedioxycholesterol

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
105 °C

Procedure

27 g of 24-oxocholesterol was dissolved in 717 ml of anhydrous benzene. To the solution were added 179 ml of ethylene glycol and 358 mg of p-toluen sulfonic acid. The mixture was stirred and heated at a bath temperature of 105° C. for 20 hours in a flask equipped with receiver capable of mesuring water in which was added a molecular sieve. Water was added to separate the reaction mixture into layers. The aqueous layer was extracted with benzene.

Workup

  1. additionwas added a molecular sieve
  2. customto separate the reaction mixture into layers
  3. extractionThe aqueous layer was extracted with benzene

Sources & evidence

ORD record
ord-68afd2783afb46ae8307a13548add226
Source dataset
uspto-grants-1981_09
Patent number
US04292249

Reaction notes

Loading…