Imidazole → 3-(2-Iodo-ethyl)-naphtho[1,2-b]furan

Participants

Reaction Steps

To a stirred solution of 2-naphtho[1,2-b]furan-3-yl ethanol (1.06 g, 5 mmol) in anhydrous THF (50 ml), triphenylphosphine (1.572 g, 6 mmol), iodine (1.518 g, 6 mmol) and imidazole (408 mg, 6 mmol) were added at room temperature. The reaction mixture was stirred at room temperature for 4 hrs and quenched with water. It was extracted with chloroform, washed well with 5% Na2S2O3 solution and the organic layer was dried over anhydrous MgSO4. It was filtered and concentrated. The residue was purified by silica-gel column chromatography by eluting it with 30% ethyl acetate:hexane. The product, namely 3-(2-iodo-ethyl)-naphtho[1,2-b]furan, was obtained as brown liquid. Yield: 1.4 g (87%); 322 (M+H).

Provenance & Evidence