Potassium Iodide → HCID 86663433, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 6-bromohexanoate (8.44 mL, 49.7 mmol) and tert-butyl 4-aminobenzoate (6.41 g, 33.2 mmol) were dissolved in N,N-dimethylformamide (33 mL), N,N-diisopropylethylamine (8.64 mL, 49.7 mmol) was added, and the mixture was stirred at 50° C. for 3 days. Potassium iodide (8.25 g, 49.7 mmol) was added, and the mixture was further stirred at 50° C. for 4 days. A saturated aqueous sodium hydrogencarbonate solution was added, and the mixture was extracted with ethyl acetate (×2). The resulting organic layer was washed with water (×3) and saturated sodium chloride solution and dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→4:1, v/v). A mixed solvent of hexane and dichloromethane was added to the resulting white solid, and the mixture was filtered to give the title compound (5.54 g; yield, 50%) as a white solid.

Provenance & Evidence