Allyltributylstannane → 5-Allyl-4-(trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-4-(trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridine (37.5 g, 138 mmol), allyltributyltin (65.8 mL, 212 mmol) and trans-dichlorobis(triphenylphosphine)palladium(II) (9.9 g, 14.1 mmol) in N,N-dimethylformamide (500 mL) was stirred at 100° C. for 1.5 hr. The reaction solution was diluted with water, and the mixture was extracted with diethyl ether. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=25/75→33/67) to give the title compound (30.9 g, yield 96%).

Provenance & Evidence