Imidazole → [(But-3-en-2-yl)oxy](tert-butyl)dimethylsilane

HRID 719393Notes

Reaction equation

HRID 719393 reaction equation
[CH3:1][CH:2]([OH:5])[CH:3]=[CH2:4].N1C=CN=C1.[CH3:11][C:12]([Si:15](Cl)([CH3:17])[CH3:16])([CH3:14])[CH3:13]>C(Cl)Cl>[C:12]([Si:15]([CH3:17])([CH3:16])[O:5][CH:2]([CH3:1])[CH:3]=[CH2:4])([CH3:14])([CH3:13])[CH3:11]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 117163-Buten-2-olHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 13307471[(But-3-en-2-yl)oxy](tert-butyl)dimethylsilaneYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of but-3-en-2-ol (5.0 g, 69.34 mmol) in CH2Cl2 (100 mL) at 0° C. was added imidazole (5.66 g, 1.2 eq) and TBSCl (10.45 g, 1.0 eq). The reaction mixture was stirred at 0° C. to rt for 3 h. Solid was filtered off, the filtrate was concentrated and passed through a short silica gel column by eluting with hexane to give tert-butyl-dimethyl-(1-methyl-allyloxy)-silane (10.86 g, 85%) as a colorless oil.

Workup

  1. filtrationSolid was filtered off
  2. concentrationthe filtrate was concentrated
  3. washby eluting with hexane

Sources & evidence

ORD record
ord-495f64c9768e43afa4840387f0a6ee57
Source dataset
uspto-grants-2006_11
Patent number
US07132432B2

Reaction notes

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