Imidazole → (2-(2-Bromothiophen-3-yl)ethoxy)(tert-butyl)dimethylsilane

HRID 507564Notes

Reaction equation

HRID 507564 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH2:7][CH2:8][OH:9].[C:10]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])([CH3:12])[CH3:11].N1C=CN=C1.O>CN(C)C=O>[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH2:7][CH2:8][O:9][Si:14]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 193595722-(2-Bromothiophen-3-yl)ethan-1-ol

Product 1

HCID 60204457(2-(2-Bromothiophen-3-yl)ethoxy)(tert-butyl)dimethylsilaneYield 84.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(2-bromothiophen-3-yl)ethanol (4.5 g, 21.8 mmol), tert-butylchlorodimethylsilane (3.16 g, 24.0 mmol) and imidazole (1.63 g, 24.0 mmol) in N,N-dimethylformamide (40 mL) was stirred at rt for 24 h. 100 mL of water was added and the mixture was extracted with diethyl ether (3×100 mL). The combined organic layers were washed with brine 3×100 mL), dried over anhydrous sodium sulfate and filtered. The solvent was removed in vacuo and the product purified by flash chromatography eluting with ethyl acetate/hexane (1:20) to give the title compound as an oil (5.9 g, 84%).

Workup

  1. extractionthe mixture was extracted with diethyl ether (3×100 mL)
  2. washThe combined organic layers were washed with brine 3×100 mL),
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed in vacuo
  6. customthe product purified by flash chromatography
  7. washeluting with ethyl acetate/hexane (1:20)

Sources & evidence

ORD record
ord-afb65328711a43388b3f07be3260d190
Source dataset
uspto-grants-2010_08
Patent number
US07786132B2

Reaction notes

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