反应详情

To a solution of 1.9 g (10 mmol) (3-bromo-pyridin-4-yl)-methanol in 50 ml dry tetrahydrofuran were added 11 ml (21 mmol) 2-propylmagnesium chloride solution (2.0 M in tetrahydrofuran). The reaction mixture was heated at reflux for 2 h. A solution of 1.9 g (10 mmol) 1-benzyl-4-piperidone in 5 ml tetrahydrofuran was added dropwise at a temperature of approximately 65° C. The reaction mixture was heated at reflux for 2 h and then quenched with water. The tetrahydrofuran was evaporated. The aqueous layer was basified to pH 10 with aqueous 2 M sodium hydroxide solution and extracted with three portions of tert-butyl methyl ether. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. Flash-chromatography gave the title compound (0.47 g, 16%) as a brown solid.

1. temperatureThe reaction mixture was heated
2. temperatureat reflux for 2 h
3. temperatureThe reaction mixture was heated
4. temperatureat reflux for 2 h
5. customquenched with water
6. customThe tetrahydrofuran was evaporated
7. extractionextracted with three portions of tert-butyl methyl ether
8. washThe combined organic layers were washed with brine
9. dry with materialdried over sodium sulfate
10. concentrationconcentrated in vacuo