تفاعل #76309

معادلة التفاعل

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

المردود 89.0%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was cooled
2. 2
   استخلاصthe reaction mixture was extracted with ether
3. 3
   غسيلThe ether layer was washed with saturated aqueous sodium bicarbonate and brine
4. 4
   تجفيفdried over MgSO4 The dried organic layer
5. 5
   أخرىwas evaporated

الإجراء التجريبي

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).

المصدر