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Potassium Phosphate, Tribasic → 2-(4-Benzyloxy-2,6-dimethylphenyl)-3-methoxycyclopent-2-enone

HRID 1193037
ノート
印刷プレビュー

反応式

HRID 1193037 の反応式
Br[C:2]1[C:3](=[O:9])[CH2:4][CH2:5][C:6]=1[O:7][CH3:8].[CH2:10]([O:17][C:18]1[CH:23]=[C:22]([CH3:24])[C:21](B(O)O)=[C:20]([CH3:28])[CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:10]([O:17][C:18]1[CH:23]=[C:22]([CH3:24])[C:21]([C:2]2[C:3](=[O:9])[CH2:4][CH2:5][C:6]=2[O:7][CH3:8])=[C:20]([CH3:28])[CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1
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

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 110954262-Bromo-3-methoxycyclopent-2-enoneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23157199(4-(Benzyloxy)-2,6-dimethylphenyl)boronic acid

生成物 1

HCID 580708252-(4-Benzyloxy-2,6-dimethylphenyl)-3-methoxycyclopent-2-enone

試薬・触媒・溶媒 2

HCID 167845
palladium(II) acetate
触媒
HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

To a suspension of 2-bromo-3-methoxycyclopent-2-enone (5.00 g, 26.0 mmol), 4-benzyloxy-2,6-dimethylphenyl boronic acid (7.20 g, 28 mmol) (described in EP1726580) and potassium phosphate (9.55 g, 45 mmol) in degassed toluene (125 ml) is added palladium (II) acetate (0.135 g, 0.6 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.492 g, 1.2 mmol). The reaction mixture is then heated at 90° C. under a nitrogen atmosphere for 4 hours, then allowed to cool to room temperature. After partitioning between ethyl acetate (500 ml) and distilled water (500 ml), the organic phase is separated and concentrated in vacuo. The crude product is purified by flash column chromatography (ethyl acetate/hexane eluant) to afford 2-(4-benzyloxy-2,6-dimethylphenyl)-3-methoxycyclopent-2-enone as a white solid.

後処理

  1. temperatureto cool to room temperature
  2. customAfter partitioning between ethyl acetate (500 ml)
  3. distillationdistilled water (500 ml)
  4. customthe organic phase is separated
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by flash column chromatography (ethyl acetate/hexane eluant)

出典と根拠

ORDレコード
ord-c54a6533cc764b0f8fe1de24e9b1e97f
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08680339B2

反応ノート

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