6-(5-Cholesten-3beta-yloxy)hexyl iodide → 6-Phthalimido-1-(5-cholesten-3beta-yloxy)hexane

HRID 851679Notes

Reaction equation

HRID 851679 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][CH2:31][CH2:32][CH2:33][CH2:34]I)[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[C:36]1(=[O:46])[NH:40][C:39](=[O:41])[C:38]2=[CH:42][CH:43]=[CH:44][CH:45]=[C:37]12.[K]>CN(C=O)C>[C:36]1(=[O:46])[N:40]([CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][O:28][C@H:18]2[CH2:19][CH2:20][C@@:21]3([CH3:22])[C:16](=[CH:15][CH2:14][C@@H:13]4[C@@H:23]3[CH2:24][CH2:25][C@@:26]3([CH3:27])[C@H:12]4[CH2:11][CH2:10][C@@H:9]3[C@H:7]([CH3:8])[CH2:6][CH2:5][CH2:4][CH:2]([CH3:3])[CH3:1])[CH2:17]2)[C:39](=[O:41])[C:38]2=[CH:42][CH:43]=[CH:44][CH:45]=[C:37]12

Participants

4

Reactant 2

HCID 128055256-(5-Cholesten-3beta-yloxy)hexyl iodideHCID 24194345Phthalimide potassium salt

Product 1

HCID 131790276-Phthalimido-1-(5-cholesten-3beta-yloxy)hexaneYield 89.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-(5-cholesten-3β-yloxy)hexyl iodide (1.0 g) and potassium phthalimide (1.0 g) in DMF (25 ml) is heated with stirring for 0.5 hours at 85°-90° C. (bath temperature). The mixture is filtered and the filtrate is evaporated in vacuo to a residue that is partitioned between chloroform and water. The organic layer is washed with aqueous sodium thiosulfate and water, dried, and evaporated to a syrup that crystallizes upon standing. Recrystallization from petroleum ether gives the title compound (0.92 g, 89%) mp 80° C.

Workup

  1. temperatureis heated
  2. filtrationThe mixture is filtered
  3. customthe filtrate is evaporated in vacuo to a residue that
  4. customis partitioned between chloroform and water
  5. washThe organic layer is washed with aqueous sodium thiosulfate and water
  6. customdried
  7. customevaporated to a syrup that
  8. customcrystallizes
  9. customRecrystallization from petroleum ether

Sources & evidence

ORD record
ord-06902dde2edb428d978387d33b8166f9
Source dataset
uspto-grants-1983_05
Patent number
US04386026

Reaction notes

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