Ammonium nitrate → 2,2,6,7-tetramethyl-5-nitro-1-benzofuran-3(2H)-one

HRID 2376282Notes

Reaction equation

HRID 2376282 reaction equation
[CH3:1][C:2]1([CH3:14])[C:6](=[O:7])[C:5]2[CH:8]=[CH:9][C:10]([CH3:13])=[C:11]([CH3:12])[C:4]=2[O:3]1.[N+:15]([O-])([O-:17])=[O:16].[NH4+]>FC(F)(F)C(O)=O.C(Cl)(Cl)Cl>[CH3:1][C:2]1([CH3:14])[C:6](=[O:7])[C:5]2[CH:8]=[C:9]([N+:15]([O-:17])=[O:16])[C:10]([CH3:13])=[C:11]([CH3:12])[C:4]=2[O:3]1

Participants

5

Reactant 2

HCID 22985Ammonium nitrateHCID 231142662,2,6,7-Tetramethyl-1-benzofuran-3(2H)-one

Product 1

HCID 231138962,2,6,7-tetramethyl-5-nitro-1-benzofuran-3(2H)-oneYield 84%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 2,2,6,7-tetramethyl-1-benzofuran-3 (2H)-one obtained in Reference Example 41 (5.20 g, 27.3 mmol) in anhydrous trifluoroacetic acid (50 mL) and chloroform (5 mL) was added ammonium nitrate (2.10 g, 32.8 mmol) at 0° C., and the mixture was stirred at the same temperature for 2 hours, and then concentrated under reduced pressure. Water was added to the residue, which was extracted with ethyl acetate. The extract was washed with water and a saturated sodium hydrogen carbonate solution, and then was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain a residue, which was purified by silica gel column chromatography (hexane:ethyl acetate=50:1) to obtain 5.40 g (yield 84%) of the title compound. Melting point: 131-132° C. (ethyl acetate-hexane).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionWater was added to the residue, which
  3. extractionwas extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materiala saturated sodium hydrogen carbonate solution, and then was dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customto obtain a residue, which
  8. customwas purified by silica gel column chromatography (hexane:ethyl acetate=50:1)

Sources & evidence

ORD record
ord-d316c671f50d4a2c8e75bac74c0aa649
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

Loading…