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

HRID 1193026ノート

反応式

HRID 1193026 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
55 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8abbc7d961744bd688b50bda39744e23
出典データセット
uspto-grants-2014_03
特許番号
US08680339B2

反応ノート

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