Imidazole → (3-Bromopropoxy)(tert-butyl)dimethylsilane

HRID 1357831Notes

Reaction equation

HRID 1357831 reaction equation
N1C=CN=C1.[C:6]([Si:10]([CH3:13])([CH3:12])Cl)([CH3:9])([CH3:8])[CH3:7].[Br:14][CH2:15][CH2:16][CH2:17][OH:18].CCOC(C)=O>C1COCC1>[Br:14][CH2:15][CH2:16][CH2:17][O:18][Si:10]([CH3:13])([CH3:12])[C:6]([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 123083-Bromo-1-propanolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Imidazole (0.52 g, 7.6 mmol) and t-butyldimethylchlorosilane (5.80 g, 38 mmol) were added successively to a solution of 1-bromo-3-propanol (5.35 g, 38 mmol) in dry THF (10 mL) at room temperature. The resulting suspension was stirred at room temperature for 20 hours. EtOAc (25 mL) was added. The solution was washed with water, dried over Na2SO4, filtered and concentrated in vacuo at room temperature. The residue was chromatographed on silica gel eluting with 1:10 EtOAc:Hex to give the title compound 2.1 g (22%) as a colorless volatile liquid. 1H NMR (300 MHz, CDCl3) δ 3.74 (t, J=5.7 Hz, 2H), 3.52 (t, J=6.5 Hz, 2H), 2.02-2.06 (mult, 2H), 0.90 (s, 9H), 0.07 (s, 6H); 13C NMR (75 MHz, CDCl3) δ 60.6, 35.7, 30.8, 26.1, −5.2.

Workup

  1. washThe solution was washed with water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo at room temperature
  5. customThe residue was chromatographed on silica gel eluting with 1:10 EtOAc

Sources & evidence

ORD record
ord-23cebc67c92e42f7af24811fdc6634de
Source dataset
uspto-grants-2003_07
Patent number
US06593347B2

Reaction notes

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