Sodium periodate → (7-methoxy-2-oxoquinolin-1(2H)-yl)acetaldehyde

HRID 657003ノート

反応式

HRID 657003 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH:14]=C)=[CH:5][CH:4]=1.I([O-])(=O)(=O)=[O:18].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH:14]=[O:18])=[CH:5][CH:4]=1

参加物

6

反応物 2

HCID 23667635Sodium periodateHCID 688097807-(Methyloxy)-1-(2-propen-1-yl)-2(1H)-quinolinone

生成物 1

HCID 59397833(7-methoxy-2-oxoquinolin-1(2H)-yl)acetaldehyde収率 71%

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a stirred solution of 7-(methyloxy)-1-(2-propen-1-yl)-2(1H)-quinolinone (4.14 g, 0.019 mol) in 1,4-dioxane (80 ml) and water (40 ml) under N2 was added sodium periodate (9.5 g; 0.044 mol) and osmium tetroxide (10 ml, 4% aqueous solution) and stirred overnight. The reaction was concentrated and partitioned in 20% MeOH/DCM (300 ml) and water (200 ml). The organic layer was dried over magnesium sulphate, filtered, and concentrated. The product was obtained after column chromatography (neat ethyl acetate) to yield g (71%) of the title compound as a green solid.

後処理

  1. concentrationThe reaction was concentrated
  2. custompartitioned in 20% MeOH/DCM (300 ml)
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was obtained after column chromatography (neat ethyl acetate)

出典と根拠

ORDレコード
ord-f361fc962ee64c8ab2923ca82377251c
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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