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

HRID 40468노트

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HRID 40468 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl촉매

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온도
90 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-d3c54b276b0a4d53ae8e78a0751849de
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530388B2

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