1H-Imidazole-2-carboxaldehyde, 1-(2-methoxyethyl)- (9CI) synthesis

Yield:558446-64-3 33%

Reaction Conditions:

with potassium carbonate;sodium iodide in N,N-dimethyl-formamide at 60; for 3 h;

Steps:

9 Reference Example 9: Synthesis of 1-(2-methoxyethyl)-1H-imidazole-2-carbaldehyde

2-Bromoethylmethylether (1.20 mL, 12.5 mmol), potassium carbonate (2.16 g, 15.6 mmol), and sodium iodide (0.468 g, 3.12 mmol) were added to a solution of 1H-imidazole-2-carbaldehyde (1.00 g, 10.4 mmol) in N,N-dimethylformamide (10.0 mL), followed by stirring at 60° C. for 3 hours. Water was added to the resultant reaction liquid, and the resultant extracted with ethyl acetate. The organic layer was washed with a 10% aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate) to obtain 1-(2-methoxyethyl)-1H-imidazole-2-carbaldehyde (0.535 g, 3.47 mmol, 33%) as a white solid. ¹H-NMR (400 MHz, CDCl₃) δ: 3.32 (3H, s), 3.67 (2H, t, J=5.0 Hz), 4.59 (2H, t, J=5.0 Hz), 7.23-7.30 (2H, m), 9.81 (1H, s).

References:

US2022/81431,2022,A1 Location in patent:Paragraph 0141-0143