반응 #78769

반응 방정식

methyl 3-[[(3-phenoxyphenyl)amino]methyl]benzoate

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

ytterbium (III) trifluoromethanesulfonate

→

methyl 3-[[(3-phenoxy-phenyl)(3,3,3-trifluoro-2-hydroxypropyl)amino]methyl]benzoate

수율 96.0%

용매

acetonitrile

water

methylene chloride

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled to room temperature
2. 2
   추출The aqueous layer was extracted with methylene chloride
3. 3
   건조dried over MgSO4
4. 4
   농축concentrated in vacuo
5. 5
   기타The crude product was purified by column chromatography on silica gel eluting with 1:9 ethyl acetate in hexane

실험 절차

EX-612B) To a mixture of methyl 3-[[(3-phenoxyphenyl)amino]methyl]benzoate (6.2 g, 0.019 mol) from EX-612A and 1,1,1-trifluoro-2,3-epoxypropane (8.58 g, 0.077 mol) in 12 mL of acetonitrile was added ytterbium (III) trifluoromethanesulfonate (1.2 g, 0.0019 mol). The resulting mixture was heated at 50° C. in a sealed glass tube for 18 h. The reaction mixture was cooled to room temperature, then diluted with water and methylene chloride. The aqueous layer was extracted with methylene chloride. The organic layers were combined, dried over MgSO4, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel eluting with 1:9 ethyl acetate in hexane to afford 8.0 g (96%) of the desired methyl 3-[[(3-phenoxy-phenyl)(3,3,3-trifluoro-2-hydroxypropyl)amino]methyl]benzoate product as a yellow oil. Anal. calcd. for C24H22F3NO4.1.4 H2O: C, 61.25; H, 5.31; N, 2.98. found: C, 61.52; H, 5.06; N, 2.89. HRMS calcd.: 446.1579 M+H]+, found: 446.1596. 1H NMR (CDCl3) δ 7.28 (m, 4H), 7.14 (t, 1H), 7.07, (m, 3H), 7.00 (s, 1H), 6.94 (d, 2H), 6.46 (dd, 1H), 6.38 (dd, 1H), 6.35 (t, 1H), 5.84 (t, 1H), 4.60 (t, 2H), 4.36 (m, 1H), 3.82 (d, 1H), 3,48 (m, 1H), 2.51 (s, 1H). 19F NMR (CDCl3) δ −79.0 (d, 3F).

출처