Imidazole → HCID 69693088, compound

HRID 967813Notes

Reaction equation

HRID 967813 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][N:10]([C:12]3[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][OH:20])=[CH:14][CH:13]=3)[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CN=C1.[CH3:26][C:27]([Si:30](Cl)([CH3:32])[CH3:31])([CH3:29])[CH3:28]>ClCCl>[Si:30]([O:20][CH2:19][CH2:18][C:15]1[CH:14]=[CH:13][C:12]([N:10]2[CH:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=[CH:9]2)=[CH:17][CH:16]=1)([C:27]([CH3:29])([CH3:28])[CH3:26])([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 22291402HCID 22291402, compound

Product 1

HCID 69693088HCID 69693088, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 2-[4-(4-phenyl-1H-imidazol-1-yl)phenyl]ethanol (5.36 g, 20.3 mmol) and imidazole (2.7 g, 40.6 mmol) in dichloromethane (100 mL) was added TBSCl (3.67 g, 24.3 mmol) at 0° C. and the reaction mixture was stirred at room temperature for 2 h. The volatile components were removed under reduced pressure, and the residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 5:1 to 2:1) to afford 5.6 g (73%) of the title compound as white solids: 1H-NMR (CDCl3)δ0.00 (6H, s), 0.88 (9H, s), 2.87 (2H, t, J=6.6 Hz), 3.84 (2H, t, J=6.6 Hz), 7.26-7.30 (2H, m), 7.35-7.44 (5H, m), 7.54-7.55 (1H, m), 7.82 (1H, br), 7.85 (2H, d, J=1.2 Hz).

Workup

  1. customThe volatile components were removed under reduced pressure
  2. customthe residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 5:1 to 2:1)

Sources & evidence

ORD record
ord-6a2ebbfb5f61494cadc97f082c09d9e2
Source dataset
uspto-grants-2005_10
Patent number
US06956050B2

Reaction notes

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