反应详情

温度

0 °C

To a stirring mixture of 4.26 g (10.7 mmol) of Ph3PCH2CH(CH3)2Br in 20 mL of THF O° C. was added 12.0 mL of n-BuLi (1.6 M in hexanes). The mixture was stirred at 0° C. for 1 h, and then 521 mg (2.82 mmol) of 5-bromonicotinaldehyde in 20 mL of THF was added. After 5-10 min. the bath was removed and stirring was continued with warming to r.t. After 1 h, the reaction was quenched with water and diluted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography 15% EtOAc/hexanes provided (E)-3-bromo-5-(3-methylbut-1-enyl)pyridine and impurity.

1. customAfter 5-10 min. the bath was removed
2. stirringstirring
3. temperaturewith warming to r.t
4. waitAfter 1 h
5. customthe reaction was quenched with water
6. additiondiluted with EtOAc
7. washThe organic layer was washed with brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customPurification by flash silica gel chromatography 15% EtOAc/hexanes