2-oxo-3-benzyl-4-methyl-7-vinyl-2H-1-benzopyrane → 2-Oxo-2H-chromene-7-carbaldehyde

HRID 253723ノート

反応式

HRID 253723 の反応式
[O:1]=[C:2]1[C:7](CC2C=CC=CC=2)=[C:6](C)[C:5]2[CH:16]=[CH:17][C:18]([CH:20]=C)=[CH:19][C:4]=2[O:3]1.I([O-])(=O)(=O)=[O:23].[Na+]>O1CCOCC1.O.CC(O)(C)C.[Os](=O)(=O)(=O)=O>[CH:20]([C:18]1[CH:19]=[C:4]2[C:5]([CH:6]=[CH:7][C:2](=[O:1])[O:3]2)=[CH:16][CH:17]=1)=[O:23]

参加物

7

反応物 2

HCID 222183942-oxo-3-benzyl-4-methyl-7-vinyl-2H-1-benzopyraneHCID 23667635Sodium periodate

生成物 1

HCID 120887742-Oxo-2H-chromene-7-carbaldehyde収率 119%

試薬・触媒・溶媒 4

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒HCID 6386tert-Butanol溶媒HCID 312751,4-Dioxane溶媒

実験手順

To the suspension of 2-oxo-3-benzyl-4-methyl-7-vinyl-2H-1-benzopyrane (16.0 g, Example 23) in dioxane (350 mL) and water (75 mL) is added osmium tetraoxide (1.45 mmol) in t-BuOH. The reaction mixture is stirred at room temperature for 30 minutes and sodium periodate (30 g) is added in portions. The solid is filtered out after 30 minutes stirring and the filtrate is partitioned between CH2Cl2 and water. Separation and the organic layer is washed further with H2O and dried over MgSO4. Evaporation of the organic solvent gives the desired 7-formyl coumarin intermediate (12.0 g).

後処理

  1. filtrationThe solid is filtered out after 30 minutes
  2. stirringstirring
  3. customthe filtrate is partitioned between CH2Cl2 and water
  4. customSeparation
  5. washthe organic layer is washed further with H2O
  6. dry with materialdried over MgSO4
  7. customEvaporation of the organic solvent

出典と根拠

ORDレコード
ord-280f5219679648988c8c8a93adb9107e
出典データセット
uspto-grants-2011_01
特許番号
US07872142B2

反応ノート

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