Imidazole → (6-Bromohexyloxy)-tert-butyldimethylsilane

HRID 1792346Notes

Reaction equation

HRID 1792346 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].N1C=CN=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>O1CCCC1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

5

Reactant 3

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

Product 1

HCID 4260352(6-Bromohexyloxy)-tert-butyldimethylsilaneYield 92.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

6-Bromo-1-hexanol (20 g, 110.42 mmol) was dissolved in dry tetrahydrofuran (700 ml) and cooled to 0° C. under argon atmosphere, to which were added imidazole (15 g, 220.84 mmol) and t-butyldimethylsilyl chloride (33 g, 220.84 mmol) and the resulting solution was stirred overnight. After the reaction was completed, the mixture was poured in ice-water and extracted with ethyl acetate. The organic solvent was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. This crude product was purified by column chromatography on silica gel, eluting with ethyl acetate:n-hexane=1:40. After removal of the solvent, 30 g of the title compound was obtained as colorless oil. (yield: 92.4%)

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic solvent was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThis crude product was purified by column chromatography on silica gel
  5. washeluting with ethyl acetate
  6. customAfter removal of the solvent

Sources & evidence

ORD record
ord-95c10823b4d04134a79b08336feba41f
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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