Reaktion #466214

Reaktionsgleichung

4-chlorophenethyl alcohol

triethylamine

methanesulfonyl chloride

2-hydroxy-4-imidazol-1-ylmethyl-benzonitrile

cesium carbonate

→

title compound

2-(4-Chlorophenyl-2-ethoxy)-4-imidazol-1-ylmethyl-benzonitrile Hydrochloride

CH3OH NH4OH

Ausbeute 0.1%

Lösungsmittel

CH2Cl2

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated in vacuo
2. 2
   workup.DISSOLUTIONdissolved in DMF (1 mL)
3. 3
   TemperaturThe reaction mixture was heated at 30° C. for 18 h
4. 4
   Sonstigepartitioned between EtOAc and H2O
5. 5
   Waschenthe aqueous layer washed with EtOAc
6. 6
   Waschenwashed with brine
7. 7
   Trocknendried (Na2SO4)
8. 8
   FiltrationFiltration and concentration to dryness

Vorschrift

4-chlorophenethyl alcohol (0.11 g, 0.67 mmol) and triethylamine (0.37 mL, 2.68 mmol) were dissolved in CH2Cl2 (5 mL) at 0° C. Then it was treated with methanesulfonyl chloride (0.207 mL, 2.68 mmol), with stirring and warming to ambient temperature, until the indicated loss of starting material. The reaction mixture was concentrated in vacuo, then dissolved in DMF (1 mL) and added to a mixture of 2-hydroxy-4-imidazol-1-ylmethyl-benzonitrile (0.10 g, 0.50 mmol) and cesium carbonate (0.33 g, 1.0 mmol) in DMF (2 mL). The reaction mixture was heated at 30° C. for 18 h, then partitioned between EtOAc and H2O, the aqueous layer washed with EtOAc, the organic layers combined, washed with brine, and dried (Na2SO4). Filtration and concentration to dryness gave the title compound after silica gel chromatography (0.1 to 0.2% CH3OH/NH4OH in CH2Cl2) and conversion to the hydrochloride salt.

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