Sodium Iodide → 2-(5-Cholesten-3beta-yloxy)ethyl iodide

HRID 128198Notes

Reaction equation

HRID 128198 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@@H:18]([O:28][CH2:29][CH2:30]Cl)[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[I-:32].[Na+]>CC(=O)CC>[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@@H:18]([O:28][CH2:29][CH2:30][I:32])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 867376273-(2-Chloroethoxy)cholest-5-ene

Product 1

HCID 867376262-(5-Cholesten-3beta-yloxy)ethyl iodideYield 77%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 2-(5-cholesten-3β-yloxy)ethyl chloride (17 g, 38 mmol) and sodium iodide (8.5 g, 57 mmol) in 2-butanone (200 ml) is heated for 5 hours under reflux. The mixture is concentrated to a residue which is partitioned between chloroform and water. The organic layer is washed with sodium thiosulfate, water, dried and evaporated to dryness. Crystallization from ether-methanol affords 2-(5-cholesten-3β-yloxy)ethyl iodide (15.8 g, 77%), m.p. 86°-88°.

Workup

  1. temperatureunder reflux
  2. concentrationThe mixture is concentrated to a residue which
  3. customis partitioned between chloroform and water
  4. washThe organic layer is washed with sodium thiosulfate, water
  5. customdried
  6. customevaporated to dryness
  7. customCrystallization from ether-methanol

Sources & evidence

ORD record
ord-24d779e9180b495aa1d5c842553ad71f
Source dataset
uspto-grants-1981_03
Patent number
US04259324

Reaction notes

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