Nitronium tetrafluoroborate → HCID 67821365, compound

HRID 487633Notes

Reaction equation

HRID 487633 reaction equation
[C:1]([C:3]1[CH:23]=[CH:22][C:6]2[O:7][C:8]([CH3:21])([CH3:20])[CH:9]=[C:10]([N:11]3[CH:16]=[C:15]([CH2:17][OH:18])[CH:14]=[CH:13][C:12]3=[O:19])[C:5]=2[CH:4]=1)#[N:2].F[B-](F)(F)F.[O:29]=[N+:30]=[O:31]>C(Cl)Cl>[C:1]([C:3]1[CH:23]=[CH:22][C:6]2[O:7][C:8]([CH3:20])([CH3:21])[CH:9]=[C:10]([N:11]3[CH:16]=[C:15]([CH2:17][O:18][N+:30]([O-:31])=[O:29])[CH:14]=[CH:13][C:12]3=[O:19])[C:5]=2[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 11073463Nitronium tetrafluoroborateHCID 19092510HCID 19092510, compound

Product 1

HCID 67821365HCID 67821365, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 10 ml of anhydrous methylene chloride, is suspended 581 mg of 6-cyano-2,2-dimethyl-4-(1,2-dihydro- 2-oxo-5-hydroxymethyl-1-pyridinyl)-2H-benzo[b]pyran obtained in Example 14. Then, 270 mg of nitronium tetrafluoroborate is added at room temperature and reacted at that temperature for 30 minutes. After stopping the reaction by adding ice water, the reaction mixture is extracted with methylene chloride, and the organic layer is washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The inorganic matter is filtered off, and the filtrate is concentrated under reduced pressure. The residue thus obtained is purified by silica gel column chromatography using 1/25 mixture of ethyl acetate/ether as a developing solvent. Thus, 328 mg of 6-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-5-nitroxymethyl-1-pyridinyl)-2H-benzo[b]pyran is obtained.

Workup

  1. customreacted at that temperature for 30 minutes
  2. customthe reaction
  3. extractionthe reaction mixture is extracted with methylene chloride
  4. washthe organic layer is washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe inorganic matter is filtered off
  7. concentrationthe filtrate is concentrated under reduced pressure
  8. customThe residue thus obtained
  9. customis purified by silica gel column chromatography
  10. addition1/25 mixture of ethyl acetate/ether as a developing solvent

Sources & evidence

ORD record
ord-358aa25146594836b2347b19cbc3f341
Source dataset
uspto-grants-1994_03
Patent number
US05296492

Reaction notes

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