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

HRID 1193027노트

반응식

HRID 1193027 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-25cb82c3ebe64374b209fef3be8ccadf
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680339B2

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