Imidazole → HCID 67429298, compound

HRID 1662755Notes

Reaction equation

HRID 1662755 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].N1C=CN=C1.[CH3:18][C:19]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])[CH3:20].O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][O:12][Si:22]([C:19]([CH3:21])([CH3:20])[CH3:18])([CH3:24])[CH3:23])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 230022542-(3-bromo-4-methoxyphenyl)ethanol

Product 1

HCID 67429298HCID 67429298, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution 45.0 g of the compound obtained in Step 216-2 in DMF (50 ml) was added 29.0 g of imidazole and 32.0 g of TBSCl, and stirred at room temperature for 16 hours. Water was added to the solution, and the resulting mixture was extracted with Et2O. The extract was dried over Na2SO4, then, the drying agent was separated by filtration and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silicagel 60; mobile phase: n-hexane/EtOAc=10/1; v/v) to obtain 62.0 g of the title compound (colorless oil).

Workup

  1. extractionthe resulting mixture was extracted with Et2O
  2. dry with materialThe extract was dried over Na2SO4
  3. customthe drying agent was separated by filtration
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by column chromatography (silicagel 60; mobile phase: n-hexane/EtOAc=10/1; v/v)

Sources & evidence

ORD record
ord-af339fd62377438eaa4e1175821867de
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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