Acetone → 5-(4-Bromo-2,6-dimethylphenyl)-4-hydroxycyclopent-2-enone

HRID 1193026노트

반응식

HRID 1193026 반응식
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[CH:13]=[CH:12][O:11][C:10]=2[CH2:14]O)=[C:4]([CH3:16])[CH:3]=1.CC(C)=[O:19]>O>[Br:1][C:2]1[CH:3]=[C:4]([CH3:16])[C:5]([CH:9]2[C:10](=[O:11])[CH:14]=[CH:12][CH:13]2[OH:19])=[C:6]([CH3:8])[CH:7]=1

참가 물질

4

반응물 2

HCID 180AcetoneHCID 66709611([4-Bromo-2,6-dimethylphenyl]furan-2-yl)methanol

생성물 1

HCID 580708555-(4-Bromo-2,6-dimethylphenyl)-4-hydroxycyclopent-2-enone

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
55 °C

실험 절차

Polyphosphoric acid (500 mg) is added to a warm (55° C.) solution of ([4-bromo-2,6-dimethylphenyl]furan-2-yl)methanol (843 mg, 3 mmol) in acetone (8 ml) and water (2 ml) and the mixture is heated at 55° C. for 24 hours. The mixture is cooled to room temperature and the acetone is removed under reduced pressure. The remaining mixture is partitioned between diethyl ether (20 ml) and water (20 ml). The aqueous phase is extracted with ether (2×50 ml), and then the organic phases are combined, washed with saturated aqueous sodium bicarbonate solution (20 ml), and brine (20 ml), dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 5-(4-bromo-2,6-dimethylphenyl)-4-hydroxycyclopent-2-enone (596 mg).

후처리

  1. temperatureThe mixture is cooled to room temperature
  2. customthe acetone is removed under reduced pressure
  3. customThe remaining mixture is partitioned between diethyl ether (20 ml) and water (20 ml)
  4. extractionThe aqueous phase is extracted with ether (2×50 ml)
  5. washwashed with saturated aqueous sodium bicarbonate solution (20 ml), and brine (20 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate is evaporated under reduced pressure
  9. customThe residue is purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-8abbc7d961744bd688b50bda39744e23
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680339B2

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