Imidazole → (5-Chloro-3-pentyloxy)(2,2-dimethylethyl)dimethylsilane {3-chloro-1-ethylpropoxy)(1,1-dimethylethyl) dimethylsilane

HRID 1722374Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][CH:4]([OH:7])[CH2:5][CH3:6].[Si:8](Cl)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].N1[CH:20]=[CH:19]N=C1.[CH3:21]N(C)C=O>>[Cl:1][CH2:2][CH2:3][CH:4]([CH2:5][CH3:6])[O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].[Cl:1][CH2:2][CH2:3][CH:4]([O:7][Si:8]([CH2:11][CH:19]([CH3:20])[CH3:21])([CH3:10])[CH3:9])[CH2:5][CH3:6]

Participants

Reactant 4

HCID 795Imidazole

HCID 6228Dimethylformamide

HCID 28928tert-Butyldimethylsilyl chloride

HCID 139240781-Chloro-3-pentanol2×

Product 1

HCID 86741753(5-Chloro-3-pentyloxy)(2,2-dimethylethyl)dimethylsilane {3-chloro-1-ethylpropoxy)(1,1-dimethylethyl) dimethylsilane

Procedure

The procedure followed is the same as that described in Example 7 substituting 5-chloropentan-3-ol {1-chloro-3-pentanol} (50 g, 0.41 moles), tert-butyldimethylsilyl chloride (71 g, 0.47 moles), imidazole (32.6 g, 0.48 moles), and dimethylformamide (150 ml). The crude product is fractionally distilled under vacuum leaving a clear, colorless oil (78 g, 0.33 moles), BP 48° C./0.1 mm.

Workup

distillationThe crude product is fractionally distilled under vacuum

Sources & evidence

ORD record: ord-491a1907af494f959c301ea90301d11c
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04855322

Reaction notes

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