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

HRID 1073538Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1073538
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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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.

Quellen und Nachweise

ORD-Eintrag
ord-8098aa7318c1488a9262e475468fb7c6
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04970199

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