反应详情

To a solution of 4.0 g (21 mmol) (2-bromo-pyridin-3-yl)-methanol in 105 ml dry tetrahydrofuran were added 22 ml (45 mmol) 2-propylmagnesium chloride solution (2.0 M in tetrahydrofuran). The reaction mixture was heated at reflux for 2 h. A solution of 3.8 g (21 mmol) 1-benzyl-4-piperidone in 22 ml tetrahydrofuran was added dropwise at a temperature of approximately 65° C. The reaction mixture was heated at reflux for 3 h and then quenched with water. The aqueous layer was basified to pH 9 with aqueous 1 M sodium hydroxide and extracted with three portions of ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. Flash-chromatography gave the title compound (1.1 g, 17%) 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 3 h
5. customquenched with water
6. extractionextracted with three portions of ethyl acetate
7. washThe combined organic layers were washed with brine
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated in vacuo