Potassium periodate → 7-Acetoxy-8-methoxycoumarin-6-acetaldehyde

HRID 1448515

Reaktionsgleichung

Reaktionsgleichung von HRID 1448515
[C:1]([O:4][C:5]1[C:14]([O:15][CH3:16])=[C:13]2[C:8]([CH:9]=[CH:10][C:11](=[O:17])[O:12]2)=[CH:7][C:6]=1[CH2:18][CH:19]=C)(=[O:3])[CH3:2].I([O-])(=O)(=O)=[O:22].[K+]>[Os](=O)(=O)(=O)=O.CCOC(C)=O.O>[C:1]([O:4][C:5]1[C:14]([O:15][CH3:16])=[C:13]2[C:8]([CH:9]=[CH:10][C:11](=[O:17])[O:12]2)=[CH:7][C:6]=1[CH2:18][CH:19]=[O:22])(=[O:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 516896Potassium periodateHCID 218145017-Acetoxy-6-allyl-8-methoxycoumarin

Produkt 1

HCID 537672567-Acetoxy-8-methoxycoumarin-6-acetaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 22728543Water ethylacetateLösungsmittel

Versuchsvorschrift

A solution of 0.274 g. (0.001 mole) of 7-acetoxy-6-allyl-8-methoxycoumarin in 10 ml. EtOAc/water, 1:1 was treated with 0.8 g. (0.0033 mole) of potassium periodate and 0.5 ml. of a 10% aqueous solution of osmium tetroxide (10 mg. OsO4 /ml H2O). The reactants were stirred at 25° for 5.0 hours. The organic layer was separated, and the aqueous phase was further extracted with ethyl acetate. The organic extracts were combined, dried over sodium sulfate, and evaporated to yield pure 7-acetoxy-8-methoxycoumarin-6-acetaldehyde as a colorless oil.

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe aqueous phase was further extracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-381186712d4749caa2f5329203fc6098
Quelldatensatz
uspto-grants-1979_12
Patentnummer
US04180659

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