Methanol → 6-Fluoro-4-oxo-3,4-dihydro-2H-1-benzopyran-2-carbonitrile

HRID 649530ノート

反応式

HRID 649530 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]=[CH:8][C:7](=[O:11])[C:6]=2[CH:12]=1.C[Si]([C:17]#[N:18])(C)C.CO>CCOCC.[I-].[Zn+2].[I-]>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH:9]([C:17]#[N:18])[CH2:8][C:7](=[O:11])[C:6]=2[CH:12]=1

参加物

6

反応物 3

HCID 887MethanolHCID 82115Trimethylsilyl cyanideHCID 6888926-Fluorochromone

生成物 1

HCID 139360026-Fluoro-4-oxo-3,4-dihydro-2H-1-benzopyran-2-carbonitrile収率 94.9%

試薬・触媒・溶媒 2

HCID 9883512zinc(II)iodide触媒HCID 3283Diethyl Ether溶媒

実験手順

To a mixture of 72.2 g (0.44 mol) of 6-fluoro-4H-1-benzopyran-4-one obtained through the process as described in said Item b and 1.39 g (4.4 mmol) of zinc iodide in 610 ml of dry ether, 101 g (1.0 mol) of trimethylsilylcyanide were added under stirring. The mixture was heated at reflux temperature for 24 hours. After cooling the reaction mixture, the solution was poured into 500 ml of methanol, stirred for one hour at room temperature and evaporated in vacuo to dryness. Resulting residue was chromatographed on silica gel, eluting with dichloromethane to give 79.7 g (94.9%) of the desired compound.

後処理

  1. customobtained through the process
  2. additionwere added
  3. temperatureThe mixture was heated
  4. temperatureat reflux temperature for 24 hours
  5. temperatureAfter cooling the reaction mixture
  6. stirringstirred for one hour at room temperature
  7. customevaporated in vacuo to dryness
  8. customResulting residue was chromatographed on silica gel
  9. washeluting with dichloromethane

出典と根拠

ORDレコード
ord-d359e4b7ccad41d6b34479c85a86e5e6
出典データセット
uspto-grants-1988_04
特許番号
US04740517

反応ノート

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