Acetophenone → Diazoacetophenone

HRID 1588049Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1588049
[H-].[Na+].[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:5])[CH3:4].C(OCC)=O.S([N:27]=[N+:28]=[N-])(C1C=CC(C)=CC=1)(=O)=O>CCOCC.C(O)C>[N+:27](=[CH:4][C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5])=[N-:28]

Komponenten

7

Edukt 4

HCID 7410AcetophenoneHCID 8025Ethyl formateHCID 13661p-Toluenesulfonyl azideHCID 24758Sodium hydride

Produkt 1

HCID 18667Diazoacetophenone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Sodium hydride (50% in oil, 0.53 g) is suspended in ether (20 ml), cooled to 0°, then treated dropwise with a mixture of acetophenone 1.2 ml) and ethyl formate (0.90 ml). The reaction is stirred 1 hr at 0° then overnight at 22°. The precipitate is filtered and washed well with ether to give a solid. The solid is suspended in ethanol (10 ml), cooled to 0°, then treated dropwise with tosyl azide (0.97 g). The reaction is stirred for 3 hrs, concentrated, dissolved in 1N sodium hydroxide and extracted with ether. The ether is washed with water, dried with sodium sulfate and concentrated to give the title compound.

Aufarbeitung

  1. temperaturecooled to 0°
  2. customovernight
  3. customat 22°
  4. filtrationThe precipitate is filtered
  5. washwashed well with ether
  6. customto give a solid
  7. temperaturecooled to 0°
  8. stirringThe reaction is stirred for 3 hrs
  9. concentrationconcentrated
  10. dissolutiondissolved in 1N sodium hydroxide
  11. extractionextracted with ether
  12. washThe ether is washed with water
  13. dry with materialdried with sodium sulfate
  14. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-cc096842c455484da7a4fd0c33a101a7
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05220021

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