Water → 5-Chloro-6-methoxypicolinaldehyde

HRID 70533

反応式

HRID 70533 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:16](OCC)=[O:17])=[N:12][C:13]=1[O:14][CH3:15].O>O1CCCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([CH:16]=[O:17])=[N:12][C:13]=1[O:14][CH3:15]

参加物

5

反応物 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 46311511Ethyl 5-chloro-6-methoxypicolinate

生成物 1

HCID 584528465-Chloro-6-methoxypicolinaldehyde収率 83%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Lithium aluminum hydride (2.54 g) was added in small portions to a solution of ethyl 5-chloro-6-methoxypyridine-2-carboxylate (22.3 g) in tetrahydrofuran (223 mL) under ice-cooling, and the mixture was stirred at the same temperature for 10 minutes. Water was added to the reaction solution under ice-cooling. After filtration through celite, the filtrate was concentrated under reduced pressure. Brine was added to the residue, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered, after which the filtrate was concentrated under reduced pressure. Manganese dioxide (116.4 g) was added to a solution of the residue in chloroform (223 mL), and the mixture was stirred at 60° C. for one hour. The reaction solution was filtered through celite, and the filtrate was concentrated under reduced pressure. The resulting residue was suspended with hexane, stirred and then filtered. The filtrate was concentrated under reduced pressure. The same operation was further repeated three times. The resulting solids were combined and dried under reduced pressure to give the title compound as a white solid (14.7 g, 83%).

後処理

  1. temperaturecooling
  2. temperaturecooling
  3. filtrationAfter filtration through celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionBrine was added to the residue
  6. extractionfollowed by extraction with ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationafter which the filtrate was concentrated under reduced pressure
  10. additionManganese dioxide (116.4 g) was added to a solution of the residue in chloroform (223 mL)
  11. stirringthe mixture was stirred at 60° C. for one hour
  12. filtrationThe reaction solution was filtered through celite
  13. concentrationthe filtrate was concentrated under reduced pressure
  14. stirringstirred
  15. filtrationfiltered
  16. concentrationThe filtrate was concentrated under reduced pressure
  17. customdried under reduced pressure

出典と根拠

ORDレコード
ord-30fa35e703934e358462d7e5a0edebf4
出典データセット
uspto-grants-2014_09
特許番号
US08822503B2

関連ノート

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