Isopropyl iodide → HCID 66971949, compound

Participants

Reaction Conditions

Reaction Steps

A 35 mL heavy-walled sealable tube was fitted with a stirbar and septa. The tritylated benzolactam from Step 4 (2.02 g, 4.83 mmol) and N,N-dimethylformamide (20 mL) were added, giving a solution that was cooled to 0° C. Sodium hydride (1.08 g, 60%/oil, 27.0 mmol) was added cautiously, giving a mixture that was stirred 5 minutes at 0° C., then removed from the cold bath and allowed to warm to room temperature. After 30 minutes, 2-iodopropane (1.0 mL, 10.0 mmol) was added, and the resulting mixture was stirred at room temperature for 18 hours. The rubber septa was then removed, the reaction vessel was sealed with a plastic screwcap, placed in an oil bath and warmed to 60° C. After 4 hours, the reaction was cooled to room temperature, diluted with H2O (100 mL) and extracted three times with diethyl ether (100 mL, then 2×50 mL). The organic extracts were combined, washed with saturated aqueous NaCl solution (50 mL), dried over MgSO4, filtered and concentrated in vacuo. The resulting oil was purified via flash chromatography on silica gel (0% to 25% ethyl acetate/hexanes linear gradient) to give the desired product.

Provenance & Evidence