Ethylene Glycol → 1-(6-Chloropyridin-3-yl)cyclopropane-1-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of (6-chloropyridin-3-yl)acetonitrile (2.00 g, 0.0131 mol), benzyltriethylammonium chloride (0.2 g, 0.0008 mol), and 1-bromo-2-chloroethane (3.26 mL, 0.0393 mol), was added sodium hydroxide aqueous solution (50%, 3 mL, 0.08 mol) drop-wise at 50° C. The mixture was stirred at 50° C. for 5 h. 1,2-ethanediol (4 mL) was added to the above mixture and stirred at 100° C. overnight. The aqueous layer was acidified to pH ˜1, and extracted with ethyl acetate. The organic layer was washed with water and brine, dried with sodium sulfate, filtered, and concentrated to afford the desired compound (2.2 g, 85%). Analytical LCMS: (M+H)+=198.0.

Provenance & Evidence