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

HRID 253723Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 253723
[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]

Komponenten

7

Edukt 2

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

Produkt 1

HCID 120887742-Oxo-2H-chromene-7-carbaldehydeAusbeute 119 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-280f5219679648988c8c8a93adb9107e
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872142B2

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