POTASSIUM DIPHOSPHATE → 2-(4'-Chloro-4-ethylbiphen-3-yl)-3-methoxycyclopent-2-enone

HRID 40468笔记

反应方程式

HRID 40468 反应方程式
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

参与物

6

反应物 3

HCID 62657POTASSIUM DIPHOSPHATEHCID 110954262-溴-3-甲氧基环戊-2-烯酮HCID 594459274'-Chloro-4-ethylbiphenyl-3-ylboronic acid

产物 1

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

试剂、催化剂与溶剂 2

HCID 167845乙酸钯(Ⅱ)催化剂HCID 112698722-双环己基膦-2',6'-二甲氧基联苯催化剂

反应条件

温度
90 °C

实验过程

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%).

后处理

  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

来源与证据

ORD记录
ord-d3c54b276b0a4d53ae8e78a0751849de
来源数据集
uspto-grants-2013_09
专利号
US08530388B2

反应笔记

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