Ammonium cerium-nitrate → HCID 69945548, compound

HRID 1859416Notes

Reaction equation

HRID 1859416 reaction equation
[CH2:1]([O:8][C@H:9]1[C@@H:14]([O:15][CH3:16])[C@H:13]([O:17]C2C=CC(OC)=CC=2)[C@H:12]2[CH2:26][O:27][C@@H:10]1[O:11]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+]([O-])([O-])=O.[Ce].[NH4+]>C1COCC1.O.ClCCl>[CH2:1]([O:8][C@H:9]1[C@@H:14]([O:15][CH3:16])[C@H:13]([OH:17])[C@H:12]2[CH2:26][O:27][C@@H:10]1[O:11]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 57418452Ammonium cerium-nitrateHCID 69945558HCID 69945558, compound

Product 1

HCID 69945548HCID 69945548, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

The above crude compound 92 is dissolved in a THF/water mixture (311 ml, 17/1) and ammonium cerium nitrate (76 g, 138 mmol) is then added at 0° C. After stirring for 30 minutes, the reaction mixture is diluted with dichloromethane (1 l) and then washed with aqueous 2% sodium hydrogen carbonate solution, and then with water. After drying, filtration and concentration, the residue is purified on silica to give compound 93 (6.63 g, 72% over two steps).

Workup

  1. additionis then added at 0° C
  2. washwashed with aqueous 2% sodium hydrogen carbonate solution
  3. customAfter drying
  4. filtrationfiltration and concentration
  5. customthe residue is purified on silica

Sources & evidence

ORD record
ord-5c7bd615923b4d4bb4a1dca8a2efcc5e
Source dataset
uspto-grants-2003_03
Patent number
US06528497B1

Reaction notes

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