Sodium ethoxide → Furo(3,2-b)pyridine

Reaction equation

[O-]CC.[Na+].C([C:8]1[O:16][C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=1)(O)=O>C(O)C>[O:16]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1

Participants

Procedure

Reaction of 30 with ethyl bromoacetate in the presence of a non-nucleophilic base such as sodium hydride in a suitable organic solvent such as tetrahydrofuran gives a compound of formula 31. Treatment of 31 with base such as sodium ethoxide in ethanol, followed by thermolysis of the resulting 2-carboxyfuro[3,2-b]pyridine of formula 32 gives furo[3,2-b]pyridine of formula 33 ((see., Shiotani, S., and Moriata, H. J. Heterocyclic Chem., 23, 665 (1986)).