Imidazole → HCID 86711274, compound

HRID 336134Notes

Reaction equation

HRID 336134 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[Br:14][CH2:15][CH:16]([OH:19])[CH:17]=[CH2:18].O>CN(C=O)C>[Br:14][CH2:15][CH:16]([O:19][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7])[CH:17]=[CH2:18]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 473501-Bromobut-3-en-2-ol

Product 1

HCID 86711274HCID 86711274, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (2.25 g) and tert-butyldimethylsilylchloride (4.75 g) were added to a solution of 1-bromo-3-buten-2-ol (4.5 g) in DMF (30 ml) at room temperature. The mixture was stirred at the same temperature for 16 hours, and water was added thereto, followed by extraction with hexane. The organic layer was washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound as a light-yellow, oily substance (7.0 g).

Workup

  1. extractionfollowed by extraction with hexane
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-580252e24eb04c6597d6f604f86dcf0f
Source dataset
uspto-grants-2014_11
Patent number
US08889666B2

Reaction notes

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