Tetrahydrofuran → (E)-3-bromo-5-(3-methylbut-1-enyl)pyridine

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence