Imidazole → HCID 59545204, compound

Participants

Reaction Steps

To an anhydrous DMF (250 mL) solution of the alcohol 4 (70.7 g, 329 mmol) was added tert-butyldimethylsilyl chloride (TBSCl, 55 g, 364 mmol) and imidazole (30 g, 441 mmol) at 0° C. The reaction was allowed to warm to room temperature, and was stirred overnight. The reaction progress was followed by TLC (5:1/hexanes:ethyl acetate). The reaction mixture was poured to a 4 L separation funnel containing diethyl ether (1.7 L), and was separated. The organics were washed with water (4×500 mL) and brine (1×250 mL), dried over magnesium sulfate. Filtration and evaporation under vacuum afforded the crude product 5 as yellowish oil (107 g, 99%), which was used directly for the next step without further purification.

Provenance & Evidence