HCID 9800193, compound → HCID 19594819, compound

HRID 612609Notes

Reaction equation

HRID 612609 reaction equation
[CH2:1]([N:3]([CH2:27][CH3:28])[CH2:4][CH2:5][O:6][C:7]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:8]=1[C:9]1[C:10]([O:25][CH3:26])=[CH:11][C:12]([O:21][CH2:22][CH2:23][CH3:24])=[CH:13][C:14]=1[C:15]2=[O:20])[CH3:2].F[B-](F)(F)F.[O:34]=[N+:35]=[O:36]>C(Cl)Cl>[CH2:27]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][O:6][C:7]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:8]=1[C:9]1[C:10]([O:25][CH3:26])=[CH:11][C:12]([O:21][CH2:22][CH2:23][CH3:24])=[C:13]([N+:35]([O-:36])=[O:34])[C:14]=1[C:15]2=[O:20])[CH3:28]

Participants

4

Reactant 2

HCID 9800193HCID 9800193, compoundHCID 11073463Nitronium tetrafluoroborate

Product 1

HCID 19594819HCID 19594819, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepare a solution of 5-(2-diethylamino-ethoxy)-4-methoxy-2-propoxy-fluoren-9-one (1.1 g, 2.9 mmole) in 100 mL anhydrous methylene chloride at -72° C. under argon while stirring. Add nitronium tetrafluoroborate (0.42 g, 3.2 mmole) in one continuous portion. Allow the mixture to warm to room temperature for 3 hours while the solution darkens. Stir an additional 2 hours, then check reaction progress with an aliquot by thin layer chromatography. Quench the reaction with water and transfer to a seperatory funnel. Retain the organic layer and filter off an insoluble red solid from the interface. Wash with water and methylene chloride. Take up the solid into 5% sodium hydroxide and stir vigorously. Extract with methylene chloride and chromatotron the organics, combine the CH2Cl2 fractions and dry over MgSO4, filter and concentrate on the rotary evaporator. Chromatograph the resulting residue, eluting with methanol/CH2Cl2 (5:95) to obtain 0.52 g (52%) of the title compound.

Workup

  1. stirringStir an additional 2 hours
  2. customreaction progress with an aliquot by thin layer chromatography
  3. customQuench
  4. customthe reaction with water and transfer to a seperatory funnel
  5. filtrationRetain the organic layer and filter off an insoluble red solid from the interface
  6. washWash with water and methylene chloride
  7. stirringstir vigorously
  8. extractionExtract with methylene chloride and chromatotron the organics,
  9. dry with materialdry over MgSO4
  10. filtrationfilter
  11. concentrationconcentrate on the rotary evaporator
  12. washChromatograph the resulting residue, eluting with methanol/CH2Cl2 (5:95)

Sources & evidence

ORD record
ord-ef6f3fd43847489998c1ed58d045db7f
Source dataset
uspto-grants-1999_12
Patent number
US06004959

Reaction notes

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