Water → 3,4-dihydro-2,2-dimethyl-6-nitro-4-(2-pyridyl)-2H-1-benzopyran

HRID 1073868Notes

Reaction equation

HRID 1073868 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[O:3]1.F[B-](F)(F)F.[O:24]=[N+:25]=[O:26].O>C(#N)C>[CH3:1][C:2]1([CH3:18])[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]2[CH:14]=[C:15]([N+:25]([O-:26])=[O:24])[CH:16]=[CH:17][C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 11073463Nitronium tetrafluoroborateHCID 198956113,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran

Product 1

HCID 198955943,4-dihydro-2,2-dimethyl-6-nitro-4-(2-pyridyl)-2H-1-benzopyranYield 15.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.32 g of 3,4-dihydro-2,2-dimethyl-4-(2-pyridyl)-2H-1-benzopyran were dissolved in 20 ml of acetonitrile and 0.73 g of nitronium tetrafluoroborate was added at room temperature. After 1 hour the mixture was poured into water and extracted with ethyl acetate. The organic extract was washed with sodium chloride solution, dried over sodium sulphate and evaporated to give an oil. This oil was chromatographed on silica gel using ethyl acetate/petroleum ether (1:4) for the elution. 245 mg of 3,4-dihydro-2,2-dimethyl-6 -nitro-4-(2-pyridyl)-2H-1-benzopyran were obtained in the form of an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customto give an oil
  7. customThis oil was chromatographed on silica gel
  8. washfor the elution

Sources & evidence

ORD record
ord-05158c735c8947cdb8e245ca3eef7735
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

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