反応 #1563875

ord-fac823e27f7d4f01835b164bc872d328

反応方程式

C=[N+]=[N-]
diazomethane
O=C(Cl)c1ccco1
furan-2-carbonyl chloride
C=[N+]=[N-]
diazomethane
[N-]=[N+]=CC(=O)c1ccco1
2-diazo-1-(furan-2-yl)ethanone
収率 49.0%

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    乾燥dried over KOH
  2. 2
    温度the resulting ethereal solution was cooled in an ice-salt bath
  3. 3
    その他The solvent was evaporated to dryness (under an argon atmosphere
  4. 4
    その他the water bath temperature below 25° C.
  5. 5
    その他was purified by column chromatography
  6. 6
    その他Evaporation of solvent

実験手順

N-Nitroso-N-methylurea (16.14 g, 61.53 mmol) was treated with a concentrated NaOH aqueous solution to produce diazomethane. The diazomethane was combined with dry ether (100 ml), dried over KOH, and the resulting ethereal solution was cooled in an ice-salt bath. A solution of furan-2-carbonyl chloride (1.6 g, 12.3 mmol) in dry ether (25 ml) was then added very slowly to the diazomethane solution. The reaction mixture was stirred overnight at room temperature. The solvent was evaporated to dryness (under an argon atmosphere, and keeping the water bath temperature below 25° C.), and the resulting crude material was purified by column chromatography using 230-400 mesh silica gel and 1% triethylamine in DCM solvent system. Evaporation of solvent yielded 2-diazo-1-(furan-2-yl)ethanone as a yellow oil (900 mg, 49%).

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US09402397B2uspto-grants-2016_08