Anisole → 1'H-1,3'-Bipyrrol-2'-yl(2-methoxyphenyl)methanone

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromoanisole (1.39 g, 7.43 mmol, 5.63 equiv) in anhydrous THF (5 mL) at −78° C., a 2.5M solution of BuLi in hexane (3 mL, 7.50 mmol, 5.68 eq.) was added dropwise, the resulting mixture was stirred for 1 h. at −78° C. to generate the lithiated anisole. In an oven-dried flask, compound (c) (270 mg, 1.32 mmol, 1 eq.) was dissolved in THF (5 mL) and cooled to −78° C., the lithiated anisole (d) was transferred into the solution containing (c) dropwise via syringe, and the resulting mixture was stirred for 1 h. at −78° C. To the reaction mixture, an aqueous solution of NH4Cl (5 mL) was added, the mixture was extracted with EtOAc, dried over anhydrous Na2SO4. The crude product was purified by flash column chromatography (10% EtOAc in Hexane) to give (e) as a light brown solid (0.30 g, 85% yield).

Provenance & Evidence