Ethylene Glycol → 2-(Cholest-5-en-3beta-yloxy)-1-ethanol

HRID 1587143Notes

Reaction equation

HRID 1587143 reaction equation
S([O:11][C@H:12]1[CH2:36][CH2:35][C@@:34]2([CH3:37])[C:14](=[CH:15][CH2:16][C@@H:17]3[C@@H:33]2[CH2:32][CH2:31][C@@:30]2([CH3:38])[C@H:18]3[CH2:19][CH2:20][C@@H:21]2[C@H:22]([CH3:29])[CH2:23][CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:13]1)(C1C=CC(C)=CC=1)(=O)=O.[CH2:39](O)[CH2:40][OH:41].O>O1CCOCC1>[CH3:28][CH:26]([CH2:25][CH2:24][CH2:23][C@H:22]([C@@H:21]1[C@:30]2([CH3:38])[C@H:18]([C@H:17]3[C@H:33]([CH2:32][CH2:31]2)[C@:34]2([CH3:37])[C:14]([CH2:13][C@@H:12]([O:11][CH2:39][CH2:40][OH:41])[CH2:36][CH2:35]2)=[CH:15][CH2:16]3)[CH2:19][CH2:20]1)[CH3:29])[CH3:27]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 962WaterHCID 109076511182-65-6

Product 1

HCID 141873352-(Cholest-5-en-3beta-yloxy)-1-ethanolYield 70.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 10 g of cholesterol tosylate and 25.3 g of ethylene glycol in 180 ml of dioxan is heated to 120° C. while stirring. The mixture is then treated with 200 ml of water and extracted with ether. The ethereal phase is washed firstly with 10% sodium carbonate solution and then with water. The organic phase is dried and evaporated. The residue is chromatographed on silica gel while eluting with ether/hexane. There are obtained 5.6 g of 2-(cholest-5-en-3β-yloxy)-1-ethanol, m.p. 92°-95° C., the starting material in Example 2q.

Workup

  1. extractionextracted with ether
  2. washThe ethereal phase is washed firstly with 10% sodium carbonate solution
  3. customThe organic phase is dried
  4. customevaporated
  5. customThe residue is chromatographed on silica gel
  6. washwhile eluting with ether/hexane

Sources & evidence

ORD record
ord-5a9fc99a148440379570455c8712019d
Source dataset
uspto-grants-1993_06
Patent number
US05215972

Reaction notes

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