Ceric ammonium nitrate → HCID 22054193, compound

HRID 1830344Notes

Reaction equation

HRID 1830344 reaction equation
C[O:2][C:3]1[C:4]([CH3:35])=[C:5]([C:26]([O:33]C)=[C:27]([O:31][CH3:32])[C:28]=1[O:29][CH3:30])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13].O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+]>C(#N)C.O>[CH3:30][O:29][C:28]1[C:3](=[O:2])[C:4]([CH3:35])=[C:5]([CH2:6][C:7]2[CH:8]=[CH:9][C:10]([O:17][CH2:18][C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])=[C:11]([CH:16]=2)[C:12]([O:14][CH3:15])=[O:13])[C:26](=[O:33])[C:27]=1[O:31][CH3:32]

Participants

5

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 22054294HCID 22054294, compound

Product 1

HCID 22054193HCID 22054193, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-(tert-butoxycarbonylmethyloxy)benzoate (1.25 g, 2.56 mmol) was dissolved in a mixed solution of acetonitrile (30 ml) and water (10 ml) and after adding thereto CAN (3.50 g, 6.39 mmol) at room temperature, the solution was stirred at room temperature for 1 hour. The reaction solution was diluted with water and then extracted with ether. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=2:1) to obtain the titled compound (0.800 g, 1.74 mmol, 68%).

Workup

  1. additionafter adding
  2. extractionextracted with ether
  3. washThe extract was washed with water
  4. customdried
  5. customthe solvent was removed by distillation
  6. customThe obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-5689e0054ab149858d7709c105b925d3
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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