Imidazole → ((5-Bromopentyl)oxy)(tert-butyl)dimethylsilane

HRID 1838901Notes

Reaction equation

HRID 1838901 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].N1C=CN=C1.[C:13]([Si:17]([CH3:20])([CH3:19])Cl)([CH3:16])([CH3:15])[CH3:14].O>O1CCCC1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][Si:17]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 1187091-Pentanol, 5-bromo-

Product 1

HCID 14381200((5-Bromopentyl)oxy)(tert-butyl)dimethylsilaneYield 89.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 28 g of the crude 5-bromo-1-pentanol in 144 ml of tetrahydrofuran is treated with 24 g of imidazole. A solution of 30.3 g of tert-butyldimethyl-chlorosilane in 46 ml of tetrahydrofuran is then added dropwise and the mixture is stirred at room temperature for 4 hours. The reaction mixture is poured into water, extracted by shaking with diethyl ether, and the organic phase is washed 4 times with water, dried over sodium sulphate and concentrated. The crude product is chromatographed on silica gel using hexane/diethyl ether. 42 g of the title compound are obtained as a colourless liquid.

Workup

  1. extractionextracted
  2. stirringby shaking with diethyl ether
  3. washthe organic phase is washed 4 times with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customThe crude product is chromatographed on silica gel

Sources & evidence

ORD record
ord-b05382d38ce34202b4e4f6aae5406b36
Source dataset
uspto-grants-2004_01
Patent number
US06677324B1

Reaction notes

Loading…