Ammonium cerium (IV) nitrate → HCID 53840937, compound

HRID 412857Notes

Reaction equation

HRID 412857 reaction equation
[C:1]([O:4][CH2:5][C@H:6]1[O:20][C@@H:10]([O:11]C2C=CC(OC)=CC=2)[C@H:9]([N:21]2[C:25](=[O:26])[C:24]3=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]3[C:22]2=[O:31])[C@@H:8]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@@H:7]1[O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)(=[O:3])[CH3:2].[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O>C(#N)C.O.C(OCC)(=O)C>[C:1]([O:4][CH2:5][C@H:6]1[O:20][CH:10]([OH:11])[C@H:9]([N:21]2[C:22](=[O:31])[C:23]3=[CH:30][CH:29]=[CH:28][CH:27]=[C:24]3[C:25]2=[O:26])[C@@H:8]([O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C@@H:7]1[O:40][CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 9869224Ammonium cerium (IV) nitrateHCID 53988496HCID 53988496, compound

Product 1

HCID 53840937HCID 53840937, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Compound 22 (9.0 g, 14.1 mmol) was dissolved in acetonitrile:water (4:1, 400 ml). Ammonium cerium (IV) nitrate (20.1 g, 36.7 mmol) was added thereto, and the mixture was stirred vigorously for 40 minutes at room temperature. The reaction mixture was diluted with ethyl acetate, washed successively with water, saturated aqueous sodium hydrogencarbonate, and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica, gel column chromatography (toluene:ethyl acetate=2.5:1) to obtain Compound 23 (6.1 g, 81%).

Workup

  1. washwashed successively with water, saturated aqueous sodium hydrogencarbonate, and saturated brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica, gel column chromatography (toluene:ethyl acetate=2.5:1)

Sources & evidence

ORD record
ord-1087e4f75d90429b8675e64d01b229a1
Source dataset
uspto-grants-2003_05
Patent number
US06562954B1

Reaction notes

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