Benzaldehyde → HCID 21186745、化合物

HRID 1384282ノート

反応式

HRID 1384282 の反応式
[CH3:1][C:2]1[N:7]=[C:6]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:5]2=[CH:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(OC(=O)C)(=O)C.[Cl-].[Zn+2].[Cl-]>[CH:18](=[C:8]1/[CH2:9][CH2:10][CH2:11][CH2:12][C:5]2[C:6]/1=[N:7][C:2]([CH3:1])=[C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:4]=2)/[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

5

反応物 2

HCID 240BenzaldehydeHCID 21186750HCID 21186750、化合物

生成物 1

HCID 21186745HCID 21186745、化合物収率 33.4%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 7918Acetic Anhydride溶媒

実験手順

Ethyl 2-methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate (1.07 g, 4.40 mmol) and benzaldehyde (583.6 mg, 5.50 mmol) were dissolved in acetic anhydride (2.0 ml), and the solution was mixed with zinc chloride (40.0 mg, 0.30 mmol) at room temperature and then heated under reflux for 36 hours. After cooling, acetic anhydride was evaporated under reduced pressure, and the thus obtained residue was mixed with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (ether:hexane=1:6-1:5) to obtain the title compound (471.4 mg, 33.4%) as pale yellow oil.

後処理

  1. temperatureheated
  2. temperatureunder reflux for 36 hours
  3. temperatureAfter cooling
  4. customacetic anhydride was evaporated under reduced pressure
  5. additionthe thus obtained residue was mixed with water
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water and saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customthe resulting residue was purified by a silica gel column chromatography (ether:hexane=1:6-1:5)

出典と根拠

ORDレコード
ord-5b670901d5d843159f95704ab0e21504
出典データセット
uspto-grants-2001_07
特許番号
US06258829B1

反応ノート

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