Diisopropylethylamine → 1-(1-{[2-(Trimethylsilyl)ethoxy]methyl}imidazol-2-yl)ethanone

Participants

Reaction Steps

To a solution of 1-(1H-imidazol-2-yl)ethanone (550 mg, 4.99 mmol), 3.18 mmol) in DCM (20 mL) was added DIPEA (1.74 ml, 9.99 mmol) and SEM chloride (0.87 ml dissolved in 5 mL DCM, 4.99 mmol). The resulting mixture was stirred at RT for 1 hr. Saturated aqueous sodium bicarbonate (10 mL) was then added and the aqueous phase was extracted with DCM (3×10 mL extractions). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to give the title intermediate as a yellow oil: 1H NMR (500 MHz, CDCl3) delta 0.00 (9H, s), 1.03-0.82 (2H, m), 2.66 (3H, s), 3.66-3.38 (2H, m), 5.76 (2H, s), 7.18 (1H, s), 7.28 (1H, s); LC-MS: m/z=+241.00 (M+H)+.

Provenance & Evidence