反応 #1447131

反応方程式

2,5-dihydro-1H-pyrrole

Triethylamine

methanesulphonyl chloride

4-bromobenzylalcohol

→

title compound

収率 71.1%

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

収率 71.1%

溶媒

ethyl acetate

ethyl acetate

dichloromethane

反応条件

後処理

1. 1
   洗浄the diluted solution was washed with an 8% aqueous sodium hydrogencarbonate solution
2. 2
   抽出The aqueous layer was extracted twice with 3 ml of ethyl acetate
3. 3
   洗浄were washed with 25% brine
4. 4
   乾燥were dried over anhydrous sodium sulfate
5. 5
   ろ過followed by filtration
6. 6
   濃縮The 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
   洗浄the diluted solution was washed thrice with 5 ml of water
10. 10
    抽出The aqueous layer was extracted twice with 5 ml of ethyl acetate
11. 11
    洗浄were washed with 25% brine
12. 12
    乾燥were dried over anhydrous sodium sulfate
13. 13
    ろ過followed by filtration
14. 14
    濃縮The filtrate was concentrated under the reduced pressure
15. 15
    その他the residue was purified by preparative thin-layer chromatography (chloroform:methanol=18:1)

実験手順

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.

出典