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

HRID 649530노트

반응식

HRID 649530 반응식
[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

참가 물질

6

반응물 3

HCID 887MethanolHCID 82115Trimethylsilyl cyanideHCID 6888926-Fluorochromone

생성물 1

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

시약·촉매·용매 2

HCID 9883512zinc(II)iodide촉매HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d359e4b7ccad41d6b34479c85a86e5e6
출처 데이터셋
uspto-grants-1988_04
특허 번호
US04740517

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