Ethyl Glycolate → Ethyl 3-hydroxyfuro[3,2-c]pyridine-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

Ethyl glycolate (7.26 g, 59.7 mmol) was added slowly into a suspension of sodium hydride (2.95 g of 60% dispersion in mineral oil, 73.8 mmol) in 85 mL of 1,2-dimethoxyethane (DME) at 0° C., and the mixture was stirred for another 30 min. A solution of ethyl 4-chloronicotinate (6.20 g, 33.4 mmol) in 20 mL of DME was added slowly into the reaction mixture at room temperature. The mixture was heated to 70° C. and maintained at that temperature overnight. The solvent was evaporated and the residue was dissolved in 100 mL of water, and washed with hexane 3 times. The pH of the water solution was adjusted to about 5 using acetic acid to pH 5, and a yellow precipitate was formed. The yellow precipitate was filtered, washed with a small amount of water (20 mL×3), and dried overnight in vacuo to give ethyl 3-hydroxyfuro[3,2-c]pyridine-2-carboxylate free base as a yellow solid (5.79 g) which was used for the next step without further purification.

Provenance & Evidence