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

HRID 1193037
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HRID 1193037 반응식
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
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참가 물질

7

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

생성물 1

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

시약·촉매·용매 2

HCID 167845
palladium(II) acetate
촉매
HCID 1140Toluene용매

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온도
90 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c54a6533cc764b0f8fe1de24e9b1e97f
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08680339B2

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