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

HRID 1906498ノート

反応式

HRID 1906498 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-e90c892401554ab399ae721e7ebb52c5
出典データセット
uspto-grants-1987_03
特許番号
US04652553

反応ノート

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