Diethylene Glycol Monomethyl Ether → HCID 58585875, compound

Participants

Reaction Steps

To the solution of diethylene glycol monomethyl ether (0.75 mL, 6.4 mmol) in DMF (10 mL) was added sodium hydride (0.26 g, 6.4 mmol). After stirring at room temperature for 30 min, 6-iodo-quinoline-3-carbonitrile (example 14c) (1.0 g, 3.18 mmol) was added to the mixture. After further stirring at room temperature for 30 min, ice water was slowly added to the reaction. The reaction was extracted with methylene chloride. The combined organic layers were successively washed with a saturated aqueous sodium bicarbonate solution and water, dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 0%-45% ethyl acetate in hexanes in 30 min) afforded 6-iodo-4-[2-(2-methoxy-ethoxy)-ethoxy]-quinoline-3-carbonitrile (0.59 g, 46%) as a light yellow solid. LC-MS m/e 399 (MH+).

Provenance & Evidence