Imidazole → HCID 18325787, compound

HRID 1251130Notes

Reaction equation

HRID 1251130 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])(C)C)([CH3:11])[CH3:10].N1[CH:21]=[CH:20]N=C1>CN(C)C=O>[CH2:12]([Si:9]([CH3:11])([CH3:10])[O:8][CH2:7][CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[CH2:15][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 794002-Thiopheneethanol

Product 1

HCID 18325787HCID 18325787, compoundYield 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-74cdf7da29954d1e8cf90a113889ba73
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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