반응 #76316

반응 방정식

N-(3-nitrophenyl)-3-(1,1,2,2-tetrafluoroethoxy) benzene-methanamine

1,1,1-trifluoro-2,3-epoxypropane

Ytterbium (III) trifluoromethane-sulfonate

→

3-[(3-nitrophenyl)[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]amino]-1,1,1-trifluoro-2-propanol

수율 45.0%

용매

acetonitrile

반응 조건

후처리

1. 1
   기타The reaction was quenched with water
2. 2
   추출extracted with ethyl acetate
3. 3
   건조The organic layer was dried over MgSO4
4. 4
   농축concentrated in vacuo
5. 5
   기타The crude product was purified by flash column chromatography on silica gel eluting with ethyl acetate:hexane 1:10

실험 절차

Ex-528B) N-(3-nitrophenyl)-3-(1,1,2,2-tetrafluoroethoxy) benzene-methanamine (3.25 g, 9.44 mmol) from EX-528A and 1,1,1-trifluoro-2,3-epoxypropane (0.895 mL, 10.4 mmol) were dissolved in 15 mL of acetonitrile. Ytterbium (III) trifluoromethane-sulfonate (0.77 g, 1.24 mmol) was added, and the stirred solution was warmed to 55° C. for 48 hours. The reaction was quenched with water and extracted with ethyl acetate. The organic layer was dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica gel eluting with ethyl acetate:hexane 1:10 to give 1.93 g (45%) of the desired 3-[(3-nitrophenyl)[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]amino]-1,1,1-trifluoro-2-propanol product as a brown oil. HRMS calcd. for C18H16F7N2O4: 457.0998 [M+H]+, found: 457.1008. 1H NMR (CDCl3) δ3.7 (dd, 1H), 3.9 (dd, 1H), 4.4 (m, 1H), 4.8 (m, 2H), 5.9 (tt, 1H), 7.0-7.2 (m, 4H), 7.3-7.4 (m, 2H), 7.6 (m, 2H).

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