Hydrogen Peroxide → 3-Acetoxy-4-(2-isopropylphenyl)-6-methyl-1-ethoxycarbonylmethyl-2-pyridinone

HRID 398378Notes

Reaction equation

HRID 398378 reaction equation
C([C:4]1[C:5](=[O:26])[N:6]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:7]([CH3:19])=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16]([CH3:18])[CH3:17])(=O)C.OO.F[C:30](F)(F)[C:31]([O:33]C(=O)C(F)(F)F)=[O:32]>C(Cl)Cl.O>[C:31]([O:33][C:4]1[C:5](=[O:26])[N:6]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:7]([CH3:19])=[CH:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16]([CH3:17])[CH3:18])(=[O:32])[CH3:30]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 9845Trifluoroacetic anhydrideHCID 230001623-Acetyl-4-(2-isopropylphenyl)-6-methyl-1-ethoxycarbonylmethyl-2-pyridinone

Product 1

HCID 230001763-Acetoxy-4-(2-isopropylphenyl)-6-methyl-1-ethoxycarbonylmethyl-2-pyridinone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3-acetyl-4-(2-isopropylphenyl)-6-methyl-1-ethoxycarbonylmethyl-2-pyridinone from step 3 above (0.65 g, 1.8 mmol) in CH2Cl2 (150 mL) at 0° C. was added 30% aqueous H2O2 (0.94 mL, 9 mmol) and trifluoroacetic anhydride (1.8 mL, 14 mmol). The resulting solution was refluxed for 1 h and then diluted with CH2Cl2 and water. The organic phase was separated, dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound (0.325 g; NMR: OCOCH3 peak at 2.05 ppm; HPLC RT=22.81 min, method B).

Workup

  1. temperatureThe resulting solution was refluxed for 1 h
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ca2dcf1adbae4f28b545e8cf09b14088
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

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