Реакция #77544

Уравнение реакции

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

1-phenyl-2-imidazolidinone

NaH

→

Compound 9

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

Растворители

dimethylformamide

Условия реакции

Обработка

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

Методика

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%).

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