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

Temperatur

-78 °C

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).

1. temperaturecooled to −78° C.
2. stirringthe resulting mixture was stirred for 1 h. at −78° C
3. extractionthe mixture was extracted with EtOAc
4. dry with materialdried over anhydrous Na2SO4
5. customThe crude product was purified by flash column chromatography (10% EtOAc in Hexane)

ORD-Eintrag

ord-3af0018848634a89881b04f280f78365

Quelldatensatz

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09340501B2