반응 #983355

반응 방정식

1-(2-fluoro-4-nitrophenyl)-4-[(trimethylsilyl)oxy]-1,2,3,6-tetrahydropyridine

allyl methyl carbonate

H2O

→

title compound

수율 70.5%

1-(2-fluoro-4-nitrophenyl)-2,3-dihydro-1H-pyridin-4-one

수율 70.5%

용매

DMSO

반응 조건

후처리

1. 1
   온도to cool to ambient temperature
2. 2
   추출The aqueous layer is extracted with EtOAc (2×800 ml)
3. 3
   세척the combined organic layers are washed with saline (800 ml)
4. 4
   건조dried over MgSO4
5. 5
   기타The solvent is removed
6. 6
   기타the residue recrystallized from EtOAc/MTBE

실험 절차

To a stirring solution of 1-(2-fluoro-4-nitrophenyl)-4-[(trimethylsilyl)oxy]-1,2,3,6-tetrahydropyridine (Step 2, 100.0 g, 322 mmol) and allyl methyl carbonate (43.6 g, 386 mmol) in DMSO (625 ml) at ambient temperature is added Pd(OAc)2 (7.20 g, 32 mmol). The resulting solution is stirred under N2 at ambient temperature overnight. H2O (1 liter) is added and solvent allowed to cool to ambient temperature. The aqueous layer is extracted with EtOAc (2×800 ml), and the combined organic layers are washed with saline (800 ml) and dried over MgSO4. The solvent is removed and the residue recrystallized from EtOAc/MTBE to afford 53.6 g (70%) of the title compound as a yellow solid, 1H NMR (CDCl3) δ 2.71 (m, 2 H), 4.06 (m, 2 H), 5.41 (d, 1 H), 7.25 (m, 1 H), 7.35 (d, 1 H), 8.08 (m, 2H).

출처