Imidazole → Methyl 2-((tert-butyldimethylsilyloxy)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

Participants

Reaction Steps

Into a flask containing a solution of methyl 2-(hydroxymethyl)-1-((2-(tri-methylsilyl)-ethoxy)methyl)-1H-imidazole-4-carboxylate (1 g, 3.49 mmol) in DMF (25 ml), imidazole (0.490 g, 6.91 mmol), catalytic DMAP and TBDMSCl (0.790 g, 5.27 mmol) were added. The resulting mixture was stirred at RT for 12 h. The reaction mixture was quenched with saturated aqueous solution of NaHCO3 and extracted with EtOAc. The organic layer was concentrated and purified by flash column chromatography. Yield 800 mg. 1H-NMR (400 MHz; DMSO-d6): δ −0.04 (s, 9H), 0.05 (s, 6H), 0.80 (t, 2H), 0.86 (s, 9H), 3.49 (t, 2H), 3.74 (s, 3H), 4.71 (s, 2H), 5.41 (s, 2H), 8.02 (s, 1H). LC-MS: [M+1]=401.10.

Provenance & Evidence