反应 #467137

反应方程式

ethyl (E)-5-[4-(trifluoromethyl)phenyl]-2-penten-4-ynoate

diisobutyl aluminum hydride toluene

→

title compound

收率 87.2%

(E)-5-[4-(Trifluoromethyl)phenyl]-2-penten-4-yn-1-ol

收率 87.2%

溶剂

toluene

反应条件

后处理

1. 1
   workup.ADDITIONwere added to the solution
2. 2
   workup.ADDITIONice was added to the mixture
3. 3
   其他the insolubles were removed by filtration
4. 4
   其他After the organic layer was dried
5. 5
   其他the crude product obtained by evaporation of the solvent
6. 6
   洗涤eluted with a mixed solvent of ethyl acetate-hexane (3:17)

实验过程

In 4 ml of toluene were dissolved 480 mg (1.79 mmol) of ethyl (E)-5-[4-(trifluoromethyl)phenyl]-2-penten-4-ynoate, and 2.38 ml (3.58 mmol) of a 1.5M diisobutyl aluminum hydride-toluene solution were added to the solution with stirring at 0° C. After 10 minutes, ice was added to the mixture and the insolubles were removed by filtration using Celite. After the organic layer was dried, the crude product obtained by evaporation of the solvent was subjected to column chromatography using 15 g of silica gel and eluted with a mixed solvent of ethyl acetate-hexane (3:17) to obtain 353 mg (yield: 87%) of the title compound as an oil.

来源