5-(2,4-Dichlorophenyl)-2-furaldehyde → 3-(3-((5-(2,4-Dichlorophenyl)furan-2-yl)methylene)-3,4,5,6-tetrahydropyridin-2-yl)pyridine

HRID 1444751

反応式

HRID 1444751 の反応式
[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

参加物

4

反応物 2

HCID 6749985-(2,4-Dichlorophenyl)-2-furaldehydeHCID 673376573-(5-Ammoniopentanoyl)pyridinium chloride

生成物 1

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

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-279a699e229440adb4be780bab589c1a
出典データセット
uspto-grants-2010_02
特許番号
US07662965B2

関連ノート

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