Water → (8-Ethyl-7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde

HRID 656906ノート

反応式

HRID 656906 の反応式
[CH2:1]([C:3]1[C:4]([F:17])=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]([CH2:13][CH:14]=C)[C:10](=[O:16])[CH:9]=[CH:8]2)[CH3:2].O.I([O-])(=O)(=O)=[O:20].[Na+]>O1CCOCC1.[Cl-].[Na+].O.CCOC(C)=O.[Os](=O)(=O)(=O)=O>[CH2:1]([C:3]1[C:4]([F:17])=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]([CH2:13][CH:14]=[O:20])[C:10](=[O:16])[CH:9]=[CH:8]2)[CH3:2]

参加物

8

反応物 3

HCID 962Water2 回HCID 23667635Sodium periodateHCID 689929808-Ethyl-7-fluoro-1-(2-propen-1-yl)-1,5-naphthyridin-2(1H)-one

生成物 1

HCID 86635314(8-Ethyl-7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde収率 91.8%

試薬・触媒・溶媒 4

HCID 30318Osmium Tetroxide触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

8-ethyl-7-fluoro-1-(2-propen-1-yl)-1,5-naphthyridin-2(1H)-one (0.181 g, 0.781 mmol) was dissolved in 1,4-dioxane (4.0 mL) and water (3.5 ml) at rt under argon. Then sodium periodate (0.418 g, 1.95 mmol) was added followed by osmium tetroxide (0.175 mL of 4% aqueous solution). After 10 mins a white precipitate came out of solution, further addition of water (2 ml) was required to re-dissolve everything. After the reaction had been left stirring at rt overnight, it was then diluted with brine (20 ml) and EtOAc (20 ml). The aqueous was then separated and washed a further with EtOAc (3×20 ml). The organic layers were then combined, dried using sodium sulphate, filtered and solvent removed to give the crude product as a yellow solid (0.168 g).

後処理

  1. customat rt
  2. dissolutionto re-dissolve everything
  3. waitAfter the reaction had been left
  4. customThe aqueous was then separated
  5. washwashed a further with EtOAc (3×20 ml)
  6. customdried
  7. filtrationfiltered
  8. customsolvent removed

出典と根拠

ORDレコード
ord-44d9be1ed69a4641af7f582606d42665
出典データセット
uspto-grants-2011_12
特許番号
US08071592B2

反応ノート

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