Imidazole → [4-(4-Bromophenyl)butoxy](tert-butyl)dimethylsilane

HRID 70568Notes

Reaction equation

HRID 70568 reaction equation
[C:1]([Si:5]([CH3:8])([CH3:7])Cl)([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][OH:25])=[CH:17][CH:16]=1.O>CN(C)C=O>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][CH2:23][CH2:24][O:25][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:8])[CH3:7])=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 282961564-(4-Bromophenyl)butan-1-ol

Product 1

HCID 58452273[4-(4-Bromophenyl)butoxy](tert-butyl)dimethylsilaneYield 103.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyldimethylchlorosilane (1.13 g) and imidazole (513 mg) were added to a solution of 4-(4-bromophenyl)butan-1-ol (1.15 g) in N,N-dimethylformamide (35 mL) under ice-cooling, and the mixture was stirred at room temperature for one hour. Water was added to the reaction solution, followed by extraction with a mixture of hexane-ethyl acetate (1:1). The organic layer was dried over sodium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:1→50:1→20:1) to give the title compound (1.78 g, quant.).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with a mixture of hexane-ethyl acetate (1:1)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:1→50:1→20:1)

Sources & evidence

ORD record
ord-af8a043c2b434b778259fbdd81951c48
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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