2-Propenoic acid, 3-[4-(trifluoromethyl)phenyl]-, ethyl ester → (E)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-ol
反応式
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:15]=[CH:14][C:6](/[CH:7]=[CH:8]/[C:9](OCC)=[O:10])=[CH:5][CH:4]=1.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]([F:16])([F:17])[C:3]1[CH:15]=[CH:14][C:6](/[CH:7]=[CH:8]/[CH2:9][OH:10])=[CH:5][CH:4]=1参加物
4
反応条件
- 温度
- 0 °C
実験手順
In 15 ml of toluene were dissolved 3.00 g (12.3 mmol) of ethyl trans-4-(trifluoromethyl)cinnamate, and 16.4 ml (24.6 mmol) of a 1.5M diisobutyl aluminum hydride-toluene solution were added to the solution with stirring at 0° C. After 20 minutes, ice-water was added to the reaction mixture and the mixture was stirred for 10 minutes, followed by removal of the insolubles by filtration using Celite. The filtrate was extracted with ethyl acetate and, after drying, the solvent was distilled off to obtain a crystalline residue. The residue was recrystallized from a mixed solvent of benzene-hexane to obtain 2.36 g (yield: 96%) of the title compound having a melting point of 53 to 55° C.