Imidazole → Tert-butyldimethyl(2-(thiophen-2-YL)ethoxy)silane

HRID 1006899Notes

Reaction equation

HRID 1006899 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][OH:8].[Si:9](Cl)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].N1C=CN=C1>CN(C)C=O>[Si:9]([O:8][CH2:7][CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 794002-Thiopheneethanol

Product 1

HCID 22503634Tert-butyldimethyl(2-(thiophen-2-YL)ethoxy)silaneYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(2-Thienyl)ethanol (2.6 g) was dissolved in N,N-dimethylformamide (20 ml), followed by the addition of t-butyldimethylsilyl chloride (3.667 g) and imidazole (1.634 g) and the mixture was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and water. The resulting organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a colorless oil (4.87 g, yield; 100%).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe resulting organic layer was washed with water
  3. dry with materialdried (over MgSO4)
  4. customevaporated
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-014e154ec0df48b6a4763ec4a9cd9224
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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