Dimethyl Sulfoxide → 2-(3-methoxy-phenoxymethyl)-1-(tetrahydro-furan-2-yl)-1H-imidazole

HRID 2101512Notes

Reaction equation

HRID 2101512 reaction equation
Cl.Cl[CH2:3][C:4]1[N:5]([CH:9]2[CH2:13][CH2:12][CH2:11][O:10]2)[CH:6]=[CH:7][N:8]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=1.CS(C)=O.C([O-])([O-])=O.[K+].[K+]>O>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=1)[O:22][CH2:3][C:4]1[N:5]([CH:9]2[CH2:13][CH2:12][CH2:11][O:10]2)[CH:6]=[CH:7][N:8]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 90073-MethoxyphenolHCID 11430Potassium CarbonateHCID 688633882-chloromethyl-1-(tetrahydro-furan-2-yl)-1H-imidazole hydrochloride

Product 1

HCID 578015312-(3-methoxy-phenoxymethyl)-1-(tetrahydro-furan-2-yl)-1H-imidazoleYield 41.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-chloromethyl-1-(tetrahydro-furan-2-yl)-1H-imidazole hydrochloride, (5.7 g, 30.6 mmol), 3-methoxyphenol (7.6 g, 61.2 mmol) and DMSO (30 mL) was added K2CO3 (12.7 g, 91.8 mmol). The mixture was stirred at ambient temperature under N2 overnight. Water (100 mL) was added and the mixture was extracted with CH2Cl2 (3×100 mL). The combined CH2Cl2 extracts were washed with 2N NaOH, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 1:2 hexane/EtOAc) to provide the desired 2-(3-methoxy-phenoxymethyl)-1-(tetrahydro-furan-2-yl)-1H-imidazole (3.49 g, 41%) as a colorless oil: ESI MS m/z 275 [C15H18N2O3+H]+.

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (3×100 mL)
  2. washThe combined CH2Cl2 extracts were washed with 2N NaOH
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (silica gel, 1:2 hexane/EtOAc)

Sources & evidence

ORD record
ord-702a2b1aff4442f89cfb3f7f52e391c6
Source dataset
uspto-grants-2009_08
Patent number
US07572921B2

Reaction notes

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