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

HRID 649530Notes

Reaction equation

HRID 649530 reaction equation
[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

Participants

6

Reactant 3

HCID 887MethanolHCID 82115Trimethylsilyl cyanideHCID 6888926-Fluorochromone

Product 1

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

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d359e4b7ccad41d6b34479c85a86e5e6
Source dataset
uspto-grants-1988_04
Patent number
US04740517

Reaction notes

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