Imidazole → (6-Bromohexyloxy)-tert-butyldimethylsilane

HRID 1616532Notes

Reaction equation

HRID 1616532 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-a5367e0b055f426685144a77e6b63b09
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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