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

HRID 2279956Notes

Reaction equation

HRID 2279956 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH2:14][CH2:15][OH:16].N1C=CN=C1>CN(C)C=O>[C:4]([Si:1]([CH3:3])([CH3:2])[O:16][CH2:15][CH2:14][C:10]1[S:9][CH:13]=[CH:12][CH:11]=1)([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 794002-Thiopheneethanol

Product 1

HCID 22503634Tert-butyldimethyl(2-(thiophen-2-YL)ethoxy)silaneYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Tert-butyldimethylsilyl chloride (15.5 g, 103 mmol) was added portionwise to a solution of 2-(2-thienyl)ethanol (11.0 g, 85.9 mmol) and imidazole (7.0 g, 103 mmol) in N,N-dimethylformamide (35 mL). The resultant solution was stirred at room temperature for 18 h. The reaction mixture was partitioned between ethyl acetate (30 mL) and water (30 mL) and the organic phases washed with water (3×50 mL). The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with 1-4% ethyl acetate in iso-hexane to give the title compound as a colourless oil (20 g, 96%).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (30 mL) and water (30 mL)
  2. washthe organic phases washed with water (3×50 mL)
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 1-4% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-747d8113bcdc4db0852ba330e4cb42ee
Source dataset
uspto-grants-2015_09
Patent number
US09133185B2

Reaction notes

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