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

HRID 523878ノート

反応式

HRID 523878 の反応式
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

参加物

8

反応物 6

HCID 7519Anisole2 回HCID 8058HexaneHCID 113582-BromoanisoleHCID 25517Ammonium ChlorideHCID 53253731ethyl 1'H-[1,3'-bipyrrole]-2'-carboxylate2 回HCID 178418339Butyllithium

生成物 1

HCID 532537321'H-1,3'-Bipyrrol-2'-yl(2-methoxyphenyl)methanone収率 85.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-3af0018848634a89881b04f280f78365
出典データセット
uspto-grants-2016_05
特許番号
US09340501B2

反応ノート

読み込み中…