2-Methoxyethanol → 2-Chloro-5-(2-methoxyethoxy)nicotinonitrile

Participants

Reaction Steps

In a 100 mL round bottom flask under N2 were dissolved triphenylphosphine (19 g, 73 mmol), 2-chloro-5-hydroxynicotinonitrile (7.5 g, 49 mmol), and 2-methoxyethanol (5.7 ml, 73 mmol) in THF (130 mL) followed by a slow addition of DEAD (27 ml, 68 mmol), and then stirred at room temperature. After 2 h the reaction showed full conversion to the desired compound. The crude mixture was purified by MPLC eluting with 100% DCM to 90% DCM: 10% MeOH to afford 2-chloro-5-(2-methoxyethoxy)nicotinonitrile (6.46 g, 63% yield) as a tan solid.

Provenance & Evidence