Sodium Iodide → 2-(2,6-Dichloropyridin-3-yl)acetaldehyde

Participants

Reaction Steps

To a solution of (E)-2,6-dichloro-3-(2-ethoxyvinyl)pyridine (890 mg, 4.08 mmol) in acetonitrile (10 ml) was added NaI (1.84 g, 12.2 mmol) and TMSCl (887 mg, 8.16 mmol). The resulting mixture was stirred at RT for 4 hours, then treated with NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to give the yellow oil 2-(2,6-dichloropyridin-3-yl)acetaldehyde (760 mg, yield: 98%). MS (M+H)+: 190.

Provenance & Evidence