Imidazole → HCID 15199977, compound

Participants

Reaction Steps

A 500 mL flask, equipped with magnetic stirrer and septum, was charged with 16.6 g crude 16 (0.095 mole), 22.1 g TBDMS-Cl (97%, 0.142 mole), 13.1 g imidazole (99%, 0.19 mole) and 240 mL DMF (distilled, added by syringe). The mixture was stirred under argon for 8 hours and then poured into 1.0 L of water and extracted with ether (3×450 mL). The combined organic extracts were dried (MgSO4), filtered and the solvent removed in vacuo to give 36.4 g of crude (orange solid). Crystallization from Et2O-pentane (1:9) and chromatography of the mother liquor concentrate on silica gel (Et2O-pentane 1:2) gave 25.0 g of 17, 91% yield.

Provenance & Evidence