反应详情

温度

5 °C

Hex-5-ynoic acid (0.1 mole) is added to a tetrahydrofuran solution of ethylmagnesium bromide (0.2 mole) maintained at 5° C. When the addition is complete, the solution is warmed to room temperature and CuCN (0.5 g) is added with stirring. After 20 minutes, a solution of benzylbromide (0.05 mole) in tetrahydrofuran is added dropwise over a one-half hour period. The reaction is maintained at room temperature until thin layer chromatography shows completion and then poured onto 1 N hydrochloric acid. This mixture is then extracted with ethyl ether and the ether layer separated. Removal of the ether gives a residue which is distilled under reduced pressure to afford the title product, 7-phenylhept-5-ynoic acid.

1. additionWhen the addition
2. temperaturethe solution is warmed to room temperature
3. temperatureThe reaction is maintained at room temperature until thin layer chromatography
4. extractionThis mixture is then extracted with ethyl ether
5. customthe ether layer separated
6. customRemoval of the ether
7. customgives a residue which
8. distillationis distilled under reduced pressure