(Trimethylsilyl)imidazole → HCID 57709150, compound

HRID 546829Notes

Reaction equation

HRID 546829 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])N1C=CN=C1.[Br:10][C:11]1[CH:12]=[C:13]([C:17]([OH:22])([CH2:20][CH3:21])[CH2:18][CH3:19])[CH:14]=[CH:15][CH:16]=1>O1CCCC1>[Br:10][C:11]1[CH:12]=[C:13]([C:17]([CH2:18][CH3:19])([O:22][Si:2]([CH3:1])([CH3:8])[CH3:9])[CH2:20][CH3:21])[CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 28925(Trimethylsilyl)imidazoleHCID 574434823-(3-Bromophenyl)pentan-3-ol

Product 1

HCID 57709150HCID 57709150, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-trimethylsilylimidazole (8.2 mL, 55.81 mol) was added to a solution of the crude 3-(3-bromo-phenyl)-pentan-3-ol in tetrahydrofuran (100 mL) in a nitrogen atmosphere at room temperature, and the mixture was stirred overnight. The reaction mixture was poured into distilled water, followed by extraction with dichloromethane. The extract was washed with brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel chromatography (n-hexane:ethyl acetate=40:1) to give the title compound as a colorless oil (8.7 g, 59% in two steps).

Workup

  1. additionThe reaction mixture was poured
  2. distillationinto distilled water
  3. extractionfollowed by extraction with dichloromethane
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-544cf9b858404d80848f9f6f4473e1c7
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

Loading…