Imidazole → Silane, [(8-bromooctyl)oxy](1,1-dimethylethyl)dimethyl-

HRID 1006747Notes

Reaction equation

HRID 1006747 reaction equation
N1C=CN=C1.[Br:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15].[C:16]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])([CH3:18])[CH3:17]>CN(C)C=O.O1CCCC1>[Br:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][Si:20]([CH3:22])([CH3:21])[C:16]([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1626071-Octanol, 8-bromo-

Product 1

HCID 10969362Silane, [(8-bromooctyl)oxy](1,1-dimethylethyl)dimethyl-Yield 88%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.55 g of imidazole were added to a solution fo 3.97 g of 8-bromo octanol in 19 ml of dimethylformamide, and over 10 minutes, 3.32 g of terbutyl chloro dimethyl silane in solution in 4.7 ml of tetrahydrofuran were added. The mixture was stirred for one hour at ambient temperature and the insoluble part was filtered off. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed on silica (eluant:cyclohexane-toluene 8-2) to obtain 5.4 g of the expected product.

Workup

  1. filtrationthe insoluble part was filtered off
  2. customThe filtrate was evaporated to dryness under reduced pressure
  3. customthe residue was chromatographed on silica (eluant:cyclohexane-toluene 8-2)

Sources & evidence

ORD record
ord-df847ec064004f2499915432bf9cfdb5
Source dataset
uspto-grants-2004_09
Patent number
US06790971B1

Reaction notes

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