Sodium Iodide → 6-(5-Cholesten-3beta-yloxy)hexyl iodide

HRID 2165882Notes

Reaction equation

HRID 2165882 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C@H:18]2[CH2:42][CH2:41][C@@:40]3([CH3:43])[C:20](=[CH:21][CH2:22][C@@H:23]4[C@@H:39]3[CH2:38][CH2:37][C@@:36]3([CH3:44])[C@H:24]4[CH2:25][CH2:26][C@@H:27]3[C@H:28]([CH3:35])[CH2:29][CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:19]2)(=O)=O)=CC=1.[I-:46].[Na+]>CC(C)=O>[I:46][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C@H:18]1[CH2:42][CH2:41][C@@:40]2([CH3:43])[C:20](=[CH:21][CH2:22][C@@H:23]3[C@@H:39]2[CH2:38][CH2:37][C@@:36]2([CH3:44])[C@H:24]3[CH2:25][CH2:26][C@@H:27]2[C@H:28]([CH3:35])[CH2:29][CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:19]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 13799772Cholest-5-en-3beta-yl 6-(p-toluenesulfonyloxy)hexyl ether

Product 1

HCID 128055256-(5-Cholesten-3beta-yloxy)hexyl iodide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of cholest-5-en-3β-yl 6-(p-toluenesulfonyloxy)hexyl ether (33 g, 51 mmol) and sodium iodide (16 g, 0.106 mol) in acetone (250 ml) was refluxed for 4 hours. The solvent was removed under reduced pressure, filtered, and the collected salts washed well with ether. The filtrate was evaporated and residual yellow oil boiled in hexanes (400 ml). The solution was decanted, concentrated to 200 ml, and stored in the refrigerator for two days. The product was filtered and the mother liquors concentrated to give a total yield of 30 g (97%), m.p. 103.5°-104.5° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. filtrationfiltered
  3. washthe collected salts washed well with ether
  4. customThe filtrate was evaporated
  5. customThe solution was decanted
  6. concentrationconcentrated to 200 ml
  7. filtrationThe product was filtered
  8. concentrationthe mother liquors concentrated
  9. customto give a total yield of 30 g (97%), m.p. 103.5°-104.5° C.

Sources & evidence

ORD record
ord-165e515b370041b89e9952fb28c64470
Source dataset
uspto-grants-1990_07
Patent number
US04942154

Reaction notes

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