Nitronium tetrafluoroborate → HCID 19895665, compound

HRID 892515Notes

Reaction equation

HRID 892515 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:7][CH:6]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[O:3]1.F[B-](F)(F)F.[O:25]=[N+:26]=[O:27]>C(#N)C>[CH3:1][C:2]1([CH3:19])[CH2:7][CH:6]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]2[CH:15]=[C:16]([N+:26]([O-:27])=[O:25])[CH:17]=[CH:18][C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 11073463Nitronium tetrafluoroborateHCID 19895670HCID 19895670, compound

Product 1

HCID 19895665HCID 19895665, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

685 mg of 3,4-dihydro-2,2-dimethyl-4-(3-methyl-2-pyridyl)-2H-1-benzopyran were dissolved in 20 ml of acetonitrile at room temperature and 360 mg of nitronium tetrafluoroborate were added. After 30 minutes the solvent was removed by evaporation and ethyl acetate and water were added. The organic phase was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:4) for the elution. There were obtained 374 mg of 3,4-dihydro-2,2-dimethyl-4-(3-methyl-2-pyridyl)-6-nitro-2H-1-benzopyran in the form of a solid of melting point 164°-165° C. after recrystallization from t-butyl methyl ether.

Workup

  1. customAfter 30 minutes the solvent was removed by evaporation and ethyl acetate and water
  2. additionwere added
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. washfor the elution

Sources & evidence

ORD record
ord-f3019c158ea7468f85a18a42f88d89c8
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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