Reaktion #77544

Reaktionsgleichung

1-Bromo-4-[(5-bromopentyl)oxy] benzene

1-phenyl-2-imidazolidinone

NaH

→

Compound 9

1-[5-(4-bromophenoxy)pentyl]-3-phenyl-2-imidazolidinone

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled in an ice bath
2. 2
   Temperaturthen cooled in ice bath
3. 3
   workup.STIRRINGthe mixture was stirred at room temperature for additional 4 hours
4. 4
   SonstigeThe reaction was quenched with MeOH
5. 5
   workup.ADDITIONSaturated aqueous NH4Cl and dichloromethane (15 mL) were added to the residue
6. 6
   SonstigeThe dichloromethane layer was separated
7. 7
   Trocknendried over MgSO4
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated
10. 10
    Sonstigepurified by column chromatography (ethyl acetate:MeOH=10:1)

Vorschrift

To a solution of 1-phenyl-2-imidazolidinone (0.10 g, 0.62 mmol) dissolved in 10 mL dimethylformamide cooled in an ice bath was added NaH (60% dispersion in mineral oil, 27.0 mg, 0.68 mmol). The mixture was stirred at room temperature for 30 minutes; then cooled in ice bath. 1-Bromo-4-[(5-bromopentyl)oxy] benzene (0.20 g, 0.62 mmol) was added, and the mixture was stirred at room temperature for additional 4 hours. The reaction was quenched with MeOH, and the solvents were pumped off. Saturated aqueous NH4Cl and dichloromethane (15 mL) were added to the residue. The dichloromethane layer was separated and dried over MgSO4, filtered, evaporated, and purified by column chromatography (ethyl acetate:MeOH=10:1) to give the product (i.e., Compound 9) as a yellow solid (0.19 g, 77%).

Quelle