Imidazole → 1-(tert-Butyldiphenylsilyloxy)propyl iodide

HRID 231603

Reaktionsgleichung

Reaktionsgleichung von HRID 231603
[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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 198228821-(tert-Butyldiphenylsilyloxy)propyl iodide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-18fda12598e749c5875a0df6582d5234
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04847306

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