Diethylene Glycol Monomethyl Ether → HCID 67508105, compound

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Reaction Steps

Neat diethylene glycol monomethyl ether (1.30 mL, 11.0 mmol, 1.5 equiv.) was added dropwise to a suspension of sodium hydride (400 mg, 60% disp., 10 mmol, 1.35 equiv.) in N,N-dimethylformamide (10 mL) over 5 minutes. The mixture was stirred at room temperature for 15 minutes, before a solution of 3-(3-iodopropyl)-2,2,5,5-tetramethylimidazolidin-4-one (2.29 g, 7.38 mmol) in N,N-dimethylformamide (10 mL) was added via cannula over 15 minutes. The mixture was then stirred overnight at room temperature. After 23 hours, the mixture was concentrated to a yellow oil which was absorbed on silica (5 g). Chromatography on silica (0-6% methanol in dichloromethane) afforded the title compound (190 mg, 8.5%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ 3.68-3.64 (m, 4H), 3.63-3.59 (m, 2H), 3.57-3.54 (m, 2H), 3.53 (t, J=6.1 Hz, 2H), 3.39 (s, 3H), 3.29-3.24 (m, 2H), 1.96-1.89 (m, 2H), 1.82 (br s, 1H), 1.41 (s, 6H), 1.32 (s, 6H); LRMS (ESI/APCI) m/z 303 [M+H]+.

Provenance & Evidence