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

HRID 523878Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[Li]CCCC.CCCCCC.C1(OC)C=CC=CC=1.[N:29]1([C:34]2[CH:38]=[CH:37][NH:36][C:35]=2[C:39](OCC)=[O:40])[CH:33]=[CH:32][CH:31]=[CH:30]1.[NH4+].[Cl-]>C1COCC1>[N:29]1([C:34]2[CH:38]=[CH:37][NH:36][C:35]=2[C:39]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[O:8][CH3:9])=[O:40])[CH:30]=[CH:31][CH:32]=[CH:33]1

Participants

Conditions

Temperature: -78 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-3af0018848634a89881b04f280f78365
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340501B2

Reaction notes

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