5-(4-Bromo-2,6-dimethylphenyl)-4-hydroxycyclopent-2-enone → 2-(4-Bromo-2,6-dimethylphenyl)cyclopent-4-ene-1,3-dione

HRID 1193027ノート

反応式

HRID 1193027 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]2[C:13](=[O:14])[CH:12]=[CH:11][CH:10]2[OH:15])=[C:4]([CH3:16])[CH:3]=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH3:16])[C:5]([CH:9]2[C:13](=[O:14])[CH:12]=[CH:11][C:10]2=[O:15])=[C:6]([CH3:8])[CH:7]=1

参加物

4

反応物 2

HCID 580708555-(4-Bromo-2,6-dimethylphenyl)-4-hydroxycyclopent-2-enoneHCID 131709961Jones' reagent

生成物 1

HCID 497653832-(4-Bromo-2,6-dimethylphenyl)cyclopent-4-ene-1,3-dione収率 94.8%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a solution of 5-(4-bromo-2,6-dimethylphenyl)-4-hydroxycyclopent-2-enone (18.33 g. 65 mmol) in acetone (200 ml) at 0° C. is added, dropwise, a solution of Jones reagent (1.67 M, 39 ml, 65 mmol) and the resulting yellow solution is stirred at 0° C. for 90 minutes. The reaction is quenched by the addition of propan-2-ol (1 ml) and stirred for a further 2 hours. Brine (300 ml) is added and the reaction is extracted with ethyl acetate (3×250 ml). The organic extracts are combined, washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is concentrated under reduced pressure. The residue is purified by column chromatography on silica gel to give 2-(4-bromo-2,6-dimethylphenyl)cyclopent-4-ene-1,3-dione (17.2 g).

後処理

  1. customThe reaction is quenched by the addition of propan-2-ol (1 ml)
  2. additionBrine (300 ml) is added
  3. extractionthe reaction is extracted with ethyl acetate (3×250 ml)
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated under reduced pressure
  8. customThe residue is purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-25cb82c3ebe64374b209fef3be8ccadf
出典データセット
uspto-grants-2014_03
特許番号
US08680339B2

反応ノート

読み込み中…