Dichloromethane → 4,5-Dichloro-2-(methyloxy)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1h-imidazole

HRID 1875234Notes

Reaction equation

HRID 1875234 reaction equation
Br[C:2]1[N:3]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[C:4]([Cl:8])=[C:5]([Cl:7])[N:6]=1.[CH3:17][O-:18].[Na+].[C-]#N.[Na+].C(Cl)Cl>CO>[Cl:7][C:5]1[N:6]=[C:2]([O:18][CH3:17])[N:3]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[C:4]=1[Cl:8]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8929Sodium CyanideHCID 10942334Sodium MethoxideHCID 586258532-Bromo-4,5-dichloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole

Product 1

HCID 687219314,5-Dichloro-2-(methyloxy)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1h-imidazoleYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2-bromo-4,5-dichloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole (0.12 g, 0.35 mmol), sodium methoxide (0.12 mL of a 25% solution in methanol, 0.53 mmol) and CuBr (0.010 g, 0.07 mmol) in methanol (0.5 mL) was heated at 100° C. for 6 h. Dilute aqueous NaCN and CH2Cl2 were added and the solution was stirred for a few minutes. The solution was extracted with EtOAc. The organic phase was dried (Na2SO4), filtered, and purified by silica gel chromatography (0-40% EtOAc/hex) to afford the title compound (0.070 g, 67%) as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 5.11 (s, 2H) 4.02 (s, 3H) 3.51-3.63 (m, 2H) 0.88-0.97 (m, 2H) −0.01 (s, 9H).

Workup

  1. extractionThe solution was extracted with EtOAc
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. custompurified by silica gel chromatography (0-40% EtOAc/hex)

Sources & evidence

ORD record
ord-51a89843899d46518667d8f77d374488
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

Loading…