5-(2,4-二氯苯基)糠醛 → 3-(3-((5-(2,4-Dichlorophenyl)furan-2-yl)methylene)-3,4,5,6-tetrahydropyridin-2-yl)pyridine

HRID 1678322

反应方程式

HRID 1678322 反应方程式
[Cl-].[NH3+:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:10]=[NH+:11][CH:12]=[CH:13][CH:14]=1)=O.[Cl-].[Cl:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[C:24]1[O:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1>C(O)(C)C>[Cl:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[C:24]1[O:30][C:27]([CH:28]=[C:6]2[CH2:5][CH2:4][CH2:3][N:2]=[C:7]2[C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[CH:26][CH:25]=1

参与物

4

反应物 2

HCID 6749985-(2,4-二氯苯基)糠醛HCID 673376573-(5-Ammoniopentanoyl)pyridinium chloride

产物 1

HCID 673373623-(3-((5-(2,4-Dichlorophenyl)furan-2-yl)methylene)-3,4,5,6-tetrahydropyridin-2-yl)pyridine收率 45.2%

试剂、催化剂与溶剂 1

HCID 3776异丙醇溶剂

反应条件

温度
80 °C

实验过程

3-(5-Ammoniopentanoyl)pyridinium chloride (103 mg, 0.41 mmol) and 5-(2,4-dichlorophenyl)furfural (128 mg, 0.53 mmol) were combined in a reaction vessel and treated with isopropanol (6 mL). The reaction vessel was sealed and the reaction was heated to 80° C. with stirring overnight. The reaction was then cooled to room temperature, concentrated under reduced pressure and treated with saturated NaHCO3(aq). This mixture was then extracted three times with EtOAc. The EtOAc extracts were washed with brine, combined, dried over Na2SO4, filtered and concentrated under reduced pressure. The recovered material was eluted through a 20 gram column of silica gel with 10.5:7:7:0.5:0.05 (700 mL) and with 7:7:7:1:0.1 (440 mL) hexane:MtBE:CH2Cl2:MeOH:NH4OH (step gradient). One sample was recovered that slowly solidified. This solid material was re-crystallized from a mixture of hot isopropanol and hexane. The crystals were recovered by vacuum filtration, washed with 20% isopropanol in hexane and then with ether, then dried under vacuum giving 71 mg (45%) of a yellow crystalline solid. LC-MS: RT=6.17 min, [M+H]+=383.0.

后处理

  1. customThe reaction vessel was sealed
  2. temperatureThe reaction was then cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additiontreated with saturated NaHCO3(aq)
  5. extractionThis mixture was then extracted three times with EtOAc
  6. washThe EtOAc extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. washThe recovered material was eluted through a 20 gram column of silica gel with 10.5:7:7:0.5:0.05 (700 mL) and with 7:7:7:1:0.1 (440 mL) hexane
  11. customOne sample was recovered that slowly solidified
  12. customThis solid material was re-crystallized from a mixture of hot isopropanol and hexane
  13. filtrationThe crystals were recovered by vacuum filtration
  14. washwashed with 20% isopropanol in hexane
  15. dry with materialwith ether, then dried under vacuum

来源与证据

ORD记录
ord-5d098c7dc5384107b64fe72f3804fe61
来源数据集
uspto-grants-2011_08
专利号
US08008499B2

关联笔记

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