ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Cesium fluoride → 2-(3,5-Dimethylbiphenyl-4-yl)-3-methoxy cyclopent-2-enone

HRID 509161
ノート
印刷プレビュー

反応式

HRID 509161 の反応式
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:10](=[O:16])[CH2:11][CH2:12][C:13]=2[O:14][CH3:15])=[C:4]([CH3:17])[CH:3]=1.[F-].[Cs+].[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:17][C:4]1[CH:3]=[C:2]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:7]=[C:6]([CH3:8])[C:5]=1[C:9]1[C:10](=[O:16])[CH2:11][CH2:12][C:13]=1[O:14][CH3:15]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 25953Cesium fluorideHCID 66827Phenylboronic AcidHCID 668681542-(4-Bromo-2,6-dimethylphenyl)-3-methoxy-cyclopent-2-enone

生成物 1

HCID 584815132-(3,5-Dimethylbiphenyl-4-yl)-3-methoxy cyclopent-2-enone収率 70.4%

試薬・触媒・溶媒 1

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒

反応条件

温度
80 °C

実験手順

To a mixture of 2-(4-bromo-2,6-dimethylphenyl)-3-methoxy-cyclopent-2-enone (1 g, 3.4 mmol), cesium fluoride (1.5 g, 9.87 mmol), phenylboronic acid (0.5 g, 4.1 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium(II) (0.44 g, 0.54 mmol) is added degassed dimethoxyethane (10 ml) and the resulting suspension is stirred under nitrogen for 45 minutes then heated at 80° C. for 4 hrs. After cooling to room temperature the reaction mixture is acidified with 1N aqueous hydrochloric acid. The aqueous phase is further extracted with ethyl acetate (3×100 ml) and then all organic fractions are combined, dried over anhydrous sodium sulphate and concentrated in vacuo. The resulting material is purified by column chromatography on silica gel to afford 2-(3,5-dimethylbiphenyl-4-yl)-3-methoxy cyclopent-2-enone (0.7 g) as a white solid.

後処理

  1. additionis added
  2. customdegassed dimethoxyethane (10 ml)
  3. temperatureAfter cooling to room temperature the reaction mixture
  4. extractionThe aqueous phase is further extracted with ethyl acetate (3×100 ml)
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe resulting material is purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-38dda0816c77469e87ef0383e8fbc78f
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09096560B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート