반응 #489780

반응 방정식

piperidine

Diethyl malonate

sodium hydride

chloroacetyl chloride

→

ethyl 4-oxo-2-piperidino-4,5-dihydrofuran-3-carboxylate

용매

tetrahydrofuran

sodium bicarbonate

반응 조건

후처리

1. 1
   온도cooled with ice bath
2. 2
   온도The mixture was refluxed for 5 min
3. 3
   온도The reaction mixture was cooled with ice bath
4. 4
   workup.STIRRINGthen stirred at 45° C. for 1 h
5. 5
   온도The reaction mixture was cooled with ice bath again
6. 6
   workup.STIRRINGstirred at ambient temperature for further 12 h
7. 7
   추출extracted with ethyl acetate for 2 times
8. 8
   추출then extracted with chloroform
9. 9
   세척The organic layer was washed with brine
10. 10
    건조dried over sodium sulfate
11. 11
    농축concentrated
12. 12
    기타The residue was purified by chromatography on silica gel(chloroform/methanol)

실험 절차

Diethyl malonate (5.0 mL, 0.033 mol) was added dropwise to a solution of sodium hydride (60% w/w in oil, 2.7 g, 0.066 mol) in anhydrous tetrahydrofuran (50 mL) that cooled with ice bath. The mixture was refluxed for 5 min. The reaction mixture was cooled with ice bath, chloroacetyl chloride (2.8 mL, 0.035 mol) was added dropwise to the reaction mixture and the mixture was stirred for 1 h then stirred at 45° C. for 1 h. The reaction mixture was cooled with ice bath again then piperidine (3.9 mL, 0.040 mol) was added dropwise and stirred at ambient temperature for further 12 h. The reaction mixture was diluted with aqueous saturated sodium bicarbonate solution, and extracted with ethyl acetate for 2 times then extracted with chloroform. The organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel(chloroform/methanol) to afford ethyl 4-oxo-2-piperidino-4,5-dihydrofuran-3-carboxylate as solid (3.5 g, y. 45%).

출처