Iodoethane → HCID 178466714, compound

Participants

Reaction Conditions

Reaction Steps

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): δ 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).

Provenance & Evidence