반응 #830360

반응 방정식

2-(4-phenylbutyl)phenol

2-(2-hydroxyethyl)-1-methylpyrrolidine

triphenylphosphine

diethyl azodicarboxylate

→

title compound

수율 38.6%

1-Methyl-2-{2-[2-(4-phenylbutyl)phenoxy]ethyl}pyrrolidine

수율 38.6%

용매

methylene chloride

반응 조건

후처리

1. 1
   온도cooling
2. 2
   농축At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
3. 3
   기타the resulting residue was partitioned between ethyl acetate and water
4. 4
   세척The organic layer was washed with a saturated aqueous solution of sodium chloride
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   농축concentrated by evaporation under reduced pressure
7. 7
   농축The resulting yellow oily concentrate
8. 8
   기타was purified by column chromatography through silica gel
9. 9
   workup.ADDITIONby volume mixture of methylene chloride and methanol as the eluent

실험 절차

522 mg of diethyl azodicarboxylate were added, whilst ice-cooling and stirring, to a solution of 226 mg of 2-(4-phenylbutyl)phenol (prepared as described in Preparation 3), 390 mg of 2-(2-hydroxyethyl)-1-methylpyrrolidine and 790 mg of triphenylphosphine in 40 ml of methylene chloride, and the resulting mixture was stirred at room temperature for 14 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure, and the resulting residue was partitioned between ethyl acetate and water. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure. The resulting yellow oily concentrate was purified by column chromatography through silica gel, using a 10:1 by volume mixture of methylene chloride and methanol as the eluent, to give 130 mg (yield 38%) of the title compound as an oil.

출처