반응 #1447131

반응 방정식

2,5-dihydro-1H-pyrrole

Triethylamine

methanesulphonyl chloride

4-bromobenzylalcohol

→

title compound

수율 71.1%

1-(4-Bromobenzyl)-2,5-dihydro-1H-pyrrole

수율 71.1%

용매

ethyl acetate

ethyl acetate

dichloromethane

반응 조건

후처리

1. 1
   세척the diluted solution was washed with an 8% aqueous sodium hydrogencarbonate solution
2. 2
   추출The aqueous layer was extracted twice with 3 ml of ethyl acetate
3. 3
   세척were washed with 25% brine
4. 4
   건조were dried over anhydrous sodium sulfate
5. 5
   여과followed by filtration
6. 6
   농축The filtrate was concentrated under the reduced pressure
7. 7
   workup.DISSOLUTIONThe residue was dissolved in 1.8 ml of N,N-dimethylformamide
8. 8
   workup.STIRRINGthe mixture was stirred at 80° C. for 3 hr
9. 9
   세척the diluted solution was washed thrice with 5 ml of water
10. 10
    추출The aqueous layer was extracted twice with 5 ml of ethyl acetate
11. 11
    세척were washed with 25% brine
12. 12
    건조were dried over anhydrous sodium sulfate
13. 13
    여과followed by filtration
14. 14
    농축The filtrate was concentrated under the reduced pressure
15. 15
    기타the residue was purified by preparative thin-layer chromatography (chloroform:methanol=18:1)

실험 절차

Triethylamine (0.135 ml, 0.958 mmol) and 60 μl (0.760 mmol) of methanesulphonyl chloride were added to a solution of 70.5 mg (0.377 mmol) of 4-bromobenzylalcohol in dichloromethane (2 ml) under ice cooling, and the mixture was stirred for 1.5 hr. The reaction solution was diluted with 10 ml of ethyl acetate, and the diluted solution was washed with an 8% aqueous sodium hydrogencarbonate solution. The aqueous layer was extracted twice with 3 ml of ethyl acetate. The organic layers were combined, were washed with 25% brine, and were dried over anhydrous sodium sulfate, followed by filtration. The filtrate was concentrated under the reduced pressure. The residue was dissolved in 1.8 ml of N,N-dimethylformamide, 87 μl of 2,5-dihydro-1H-pyrrole (70% purity, 0.793 mmol) was added to the solution, and the mixture was stirred at 80° C. for 3 hr. The reaction solution was diluted with 10 ml of ethyl acetate, and the diluted solution was washed thrice with 5 ml of water. The aqueous layer was extracted twice with 5 ml of ethyl acetate. The organic layers were combined, were washed with 25% brine, and were dried over anhydrous sodium sulfate, followed by filtration. The filtrate was concentrated under the reduced pressure, and the residue was purified by preparative thin-layer chromatography (chloroform:methanol=18:1) to give 63.8 mg (yield 71%) of the title compound.

출처