Imidazole → (3-Bromopropoxy)(tert-butyl)dimethylsilane

HRID 726092Notes

Reaction equation

HRID 726092 reaction equation
N1C=CN=C1.[Br:6][CH2:7][CH2:8]CCCCCCO.[C:16]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])([CH3:18])[CH3:17].CN(C)[CH:26]=[O:27]>O1CCCC1>[Br:6][CH2:7][CH2:8][CH2:26][O:27][Si:20]([CH3:22])([CH3:21])[C:16]([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 1626071-Octanol, 8-bromo-

Product 1

HCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.55 g of imidazole were added to a solution of 3.97 g of 8-bromo octanol in 19 ml of dimethylformamide, and over 10 minutes, 3.32 g of tertbutyl chloro dimethyl silane in solution in 4,7 ml 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-5b62c6ec34904fe4be95eca558854a2d
Source dataset
uspto-grants-1998_01
Patent number
US05707982

Reaction notes

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