반응 #48589

반응 방정식

3,4-Dinitrofluorobenzene

4-hydroxy-1-methylpiperidine

sodium hydride

→

4-(3,4-dinitro-phenoxy)-1-methyl-piperidine

용매

THF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added in several small portions
2. 2
   기타partitioned between ethyl acetate and water
3. 3
   세척the organic phase washed with brine
4. 4
   건조dried (MgSO4)
5. 5
   세척eluting with 5% MeOH/DCM

실험 절차

3,4-Dinitrofluorobenzene (1.86 g, 10 mmol) and 4-hydroxy-1-methylpiperidine (1.38 g, 12 mmol) were dissolved in THF (20 ml) and stirred at ambient temperature while sodium hydride (60% dispersion in mineral oil, 0.40 g, 10 mmol) was added in several small portions. The reaction mixture was stirred for one hour and then reduced in vacuo, partitioned between ethyl acetate and water, and the organic phase washed with brine, dried (MgSO4) and reduced in vacuo. The resulting residue was subject to column chromatography, eluting with 5% MeOH/DCM to give a yellow solid (1.76 g, 2:1 ratio of 4-(3,4-dinitro-phenoxy)-1-methyl-piperidine and a 4-(4-fluoro-2-nitro-phenoxy)-1-methyl-piperidine).

출처