Acetophenone → Diazoacetophenone

HRID 1588049노트

반응식

HRID 1588049 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 18667Diazoacetophenone

시약·촉매·용매 2

HCID 702Ethanol용매HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cc096842c455484da7a4fd0c33a101a7
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05220021

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