반응 #76309

반응 방정식

water

3-[[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]amino]phenol

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

ytterbium trifluoromethanesulfonate

→

3-[[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl](3,3,3-trifluoro-2hydroxypropyl)amino]phenol

수율 89.0%

용매

acetonitrile

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled
2. 2
   추출the reaction mixture was extracted with ether
3. 3
   세척The ether layer was washed with saturated aqueous sodium bicarbonate and brine
4. 4
   건조dried over MgSO4 The dried organic layer
5. 5
   기타was evaporated

실험 절차

A solution of 3-[[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]amino]phenol (11.0 g, 34.9 mmol), 3,3,3-trifluoro-1,2-epoxypropane (4.5 mL, 52.4 mmol) and ytterbium trifluoromethanesulfonate (2.2 g, 10 mol %) in 20 mL of acetonitrile was heated at 50° C. in a sealed glass tube for 16 h. The reaction mixture was cooled, water was added, and the reaction mixture was extracted with ether. The ether layer was washed with saturated aqueous sodium bicarbonate and brine and dried over MgSO4 The dried organic layer was evaporated to give 8.07 g (89%) of the desired 3-[[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl](3,3,3-trifluoro-2hydroxypropyl)amino]phenol product as a yellow oil. HRMS calcd. for C18H17F7NO3: 428.1097 [M+H]+, found: 428.1104. 1H NMR (CDCl3) δ3.58 (dd, 1H), 3.88 (dd, 1H), 4.39 (m, 1H), 4.68 (s, 2H), 5.91 (tt, 1H), 6.25-6.37 (m, 3H), 7.07-7.14 (m, 4H), 7.35 (t, 1H).

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