Imidazole → 1-(tert-Butyldiphenylsilyloxy)propyl iodide

HRID 728691Notes

Reaction equation

HRID 728691 reaction equation
[I:1][CH2:2][CH2:3][CH2:4]O.N1C=CN=C1.[C:11]([Si:15](Cl)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:14])([CH3:13])[CH3:12].[OH2:29]>CN(C)C=O>[Si:15]([O:29][CH:2]([I:1])[CH2:3][CH3:4])([C:11]([CH3:14])([CH3:13])[CH3:12])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 693903-Iodo-1-propanolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 198228821-(tert-Butyldiphenylsilyloxy)propyl iodide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 3-iodo-1-propanol (4.3 g, 23 mmol) and imidazole (3.74 g, 55 mmol) in dimethylformamide (20 ml) was added tert-butylchlorodiphenylsilane (6.8 g, 24.7 mmol) at ambient temperature and the reaction mixture was stirred for 20 hours. The reaction mixture was then poured into cold water. The combined extracts were washed with dilute hydrochloric acid, 5 percent sodium bicarbonate dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography over silica gel eluted with CH2Cl2 :hexane (1:5, v:v) and further by distillation to afford the desired product as a colorless oil: b.p. 134-5° C./0.01 mmHg.

Workup

  1. washThe combined extracts were washed with dilute hydrochloric acid, 5 percent sodium bicarbonate
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography over silica gel
  5. washeluted with CH2Cl2 :hexane (1:5, v:v) and further by distillation

Sources & evidence

ORD record
ord-77c496daee1e4d92884d6bef93db6bee
Source dataset
uspto-grants-1991_09
Patent number
US05049696

Reaction notes

Loading…