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

HRID 2267340Notes

Reaction equation

HRID 2267340 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-butylchloro-dimethylsilane (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 (3×00 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 (3×00 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-05cc8a37d2bd448ebba6192bc39edd02
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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