Imidazole → 4,5-Dichloro-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole

HRID 1875119Notes

Reaction equation

HRID 1875119 reaction equation
N1C=CN=C1.[Cl:6][C:7]1[N:8]=[C:9]([CH2:21][OH:22])[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:11]=1[Cl:12].Cl[Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].[NH4+].[Cl-]>C(Cl)Cl>[Cl:6][C:7]1[N:8]=[C:9]([CH2:21][O:22][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:18])([CH3:19])[CH3:20])[C:11]=1[Cl:12]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 68487065HCID 68487065, compound

Product 1

HCID 684838634,5-Dichloro-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazoleYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Imidazole (282 mg, 4.14 mmol) was added to a solution of [4,5-dichloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazol-2-yl]methanol (614 mg, 2.07 mmol) and chloro(1,1-dimethylethyl)dimethylsilane (345 mg, 2.28 mmol) in DCM (8 mL) at RT under N2. The mixture was stirred overnight. Aqueous NH4Cl was then added. Extracted with DMC and the extracts were dried over sodium sulfate and concentrated. The residue was purified by column chromatography (0-10% EtOAc in hexane) to give the title compound (845 mg, 99%) as a colorless oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 5.42 (2H, s) 4.74 (2H, s) 3.53-3.59 (2H, m) 0.87-0.95 (11H, m) 0.09 (6H, s) 0.00 (9H, s). LCMS: m/z 411 (M+1).

Workup

  1. extractionExtracted with DMC
  2. dry with materialthe extracts were dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (0-10% EtOAc in hexane)

Sources & evidence

ORD record
ord-cedab6d9959d4b52ab73d2a341917eca
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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