3-ethoxypyridin-2-ol

To a solution of 2, 3-dihydroxypyridine (5.0 g, 45.0 mmol, 1.0 equiv) and sodium tert-butoxide (4.33 g, 45.0 mmol, 1.0 equiv) in methanol (25 mL) was added ethyl iodide (5.21 mL, 7.72 g, 49.5 mmol, 1.1 equiv) and the reaction mixture heated to 100° C. under microwave irradiation for 20 min. The solvent was removed and the reaction product dissolved in dichloromethane (50 mL), the obtained suspension filtered and the organic phase concentrated by evaporation under reduced pressure. The crude material was purified by column chromatography on silica eluting with dichloromethane/methanol (9:1) yielding 3.0 g (41percent) of the title compound. A mixture of To a solution of 2, 3-dihydroxypyridine (5.0 g, 45.0 mmol, 1.0 equiv) and sodium tert-butoxide (4.33 g, 45.0 mmol, 1.0 equiv) in methanol (25 mL) was added ethyl iodide (5.21 mL, 7.72 g, 49.5 mmol, 1.1 equiv) and the reaction mixture heated to 100 C. under microwave irradiation for 20 min. The solvent was removed and the reaction product dissolved in dichloromethane (50 mL), the obtained suspension filtered and the organic phase concentrated by evaporation under reduced pressure. The crude material was purified by column chromatography on silica eluting with dichloromethane/methanol (9:1) yielding 3.0 g (41%) of the title compound. 1H NMR (300 MHz, CDCl3): delta 1.50 (t, J=7.0 Hz, 3H), 4.05 (q, J=7.0 Hz, 2H), 6.20 (t, J=7.1 Hz, 1H), 6.76 (dd, J=7.4 Hz, J=1.3 Hz, 1H), 7.05 (dd, J=6.5 Hz, J=1.3 Hz, 1H), 13.36 (br s, 1H).

Molecular Weight:139.15
XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:139.063328530
Monoisotopic Mass:139.063328530
Topological Polar Surface Area:38.3
Heavy Atom Count:10
Complexity:194
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes