Reaction #88890

Reaction equation

ethyl 2-chloronicotinate

tributyl(1-ethoxyvinyl)tin

→

title compound

ethyl 2-(1-ethoxyvinyl)nicotinate

Solvents

toluene

Conditions

Workup

1. 1
   OtherThe solvent was evaporated under reduced pressure
2. 2
   Otherthe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)
3. 3
   Otherpurified by silica gel column chromatography (ethyl acetate/hexane)

Procedure

To a mixture of ethyl 2-chloronicotinate (23 g), tributyl(1-ethoxyvinyl)tin (64 mL) and toluene (400 mL) was added tetrakis(triphenylphosphine)palladium(0) (7.3 g), and the mixture was stirred overnight at 80° C. under an argon atmosphere. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane), and then purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (27 g).

Source