[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6](=[O:8])[CH3:7].CCN(C(C)C)C(C)C.[CH3:18][Si:19]([CH2:22][CH2:23][O:24][CH2:25]Cl)([CH3:21])[CH3:20].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:18][Si:19]([CH3:21])([CH3:20])[CH2:22][CH2:23][O:24][CH2:25][N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6](=[O:8])[CH3:7]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)+.
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