Imidazole → (6-Bromohexyloxy)-tert-butyldimethylsilane

HRID 1443645Notes

Reaction equation

HRID 1443645 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16].N1C=CN=C1>CN(C)C=O.O>[Br:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 779706-Bromo-1-hexanol

Product 1

HCID 4260352(6-Bromohexyloxy)-tert-butyldimethylsilaneYield 98.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Add a solution of tert-butyldimethylsilyl chloride (5.0 g, 33.1 mmol) in dimethylforamide (DMF) (70 mL) dropwise over 15 minutes to a solution of 6-bromohexanol (5.0 g, 27.6 mmol) and imidazole (4.7 g, 69 mmol) in DMF (80 mL) at 0° C. under nitrogen protection and stir the mixture for another 3.5 hours. Dilute the mixture with water (400 mL) and extract with diethyl ether (3×150 mL). Dry the combined organic extracts over sodium sulfate and remove the solvent under reduced pressure. Purify the crude product by flash column chromatography on silica gel, eluting with ethyl acetate/hexanes (1:19), to provide (6-bromohexyloxy)-tert-butyldimethylsilane (8.05 g, 98%).

Workup

  1. extractionextract with diethyl ether (3×150 mL)
  2. dry with materialDry the combined organic extracts over sodium sulfate
  3. customremove the solvent under reduced pressure
  4. customPurify the crude product by flash column chromatography on silica gel
  5. washeluting with ethyl acetate/hexanes (1:19)

Sources & evidence

ORD record
ord-71ab0a6ee7be4561ba2b8575f3308839
Source dataset
uspto-grants-2010_02
Patent number
US07662771B2

Reaction notes

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