Potassium Phosphate, Tribasic → 2-(4'-Chloro-4-ethylbiphen-3-yl)-3-methoxycyclopent-2-enone

HRID 40468ノート

反応式

HRID 40468 の反応式
Br[C:2]1[C:3](=[O:9])[CH2:4][CH2:5][C:6]=1[O:7][CH3:8].[Cl:10][C:11]1[CH:27]=[CH:26][C:14]([C:15]2[CH:16]=[CH:17][C:18]([CH2:24][CH3:25])=[C:19](B(O)O)[CH:20]=2)=[CH:13][CH:12]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[Cl:10][C:11]1[CH:27]=[CH:26][C:14]([C:15]2[CH:20]=[CH:19][C:18]([CH2:24][CH3:25])=[C:17]([C:2]3[C:3](=[O:9])[CH2:4][CH2:5][C:6]=3[O:7][CH3:8])[CH:16]=2)=[CH:13][CH:12]=1

参加物

6

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 110954262-Bromo-3-methoxycyclopent-2-enoneHCID 594459274'-Chloro-4-ethylbiphenyl-3-ylboronic acid

生成物 1

HCID 585028162-(4'-Chloro-4-ethylbiphen-3-yl)-3-methoxycyclopent-2-enone収率 75.5%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl触媒

反応条件

温度
90 °C

実験手順

To a stirred suspension of 2-bromo-3-methoxycyclopent-2-enone (1.0 g, 5.23 mmol), 4′-chloro-4-ethylbiphen-3-ylboronic acid (2.03 g, 7.80 mmol) and potassium phosphate (2.23 g, 10.50 mmol) in anhydrous, degassed toluene (25 ml) under an atmosphere of nitrogen is added palladium(II)acetate (24 mg, 0.105 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (86 mg, 0.209 mmol). The reaction is heated at 90° C. for 4 hours and then allowed to cool to room temperature, quenched with water (40 ml) and extracted with ethyl acetate (3×30 ml). The organic extracts are combined, washed with brine (15 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 2-(4′-chloro-4-ethylbiphen-3-yl)-3-methoxycyclopent-2-enone (1.29 g, 75%).

後処理

  1. customdegassed toluene (25 ml) under an atmosphere of nitrogen
  2. temperatureto cool to room temperature
  3. customquenched with water (40 ml)
  4. extractionextracted with ethyl acetate (3×30 ml)
  5. washwashed with brine (15 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-d3c54b276b0a4d53ae8e78a0751849de
出典データセット
uspto-grants-2013_09
特許番号
US08530388B2

反応ノート

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