m-Chloroperbenzoic acid → HCID 136344256, compound

HRID 1669377Notes

Reaction equation

HRID 1669377 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([CH3:9])[C:4](=[O:10])[C:3]=1[C:11](=[O:27])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][S:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH:15]=1.ClC1C=CC=C(C(OO)=[O:36])C=1>C(Cl)Cl>[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([CH3:9])[C:4](=[O:10])[C:3]=1[C:11](=[O:27])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][S:21]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[O:36])[CH:15]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 136344257HCID 136344257, compound

Product 1

HCID 136344256HCID 136344256, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.17 g of 4-hydroxy-3-[3-[3-[(methoxycarbonylmethylthio)methyl]phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone in 4 ml of methylene chloride was added 0.076 g of m-chloroperbenzoic acid in portions under ice-cooling. After stirred under ice-cooling, the solvent was distilled off under reduced pressure, water was added to the residue, this was extracted with ethyl acetate, washed with an aqueous sodium bicarbonate solution, and further washed with an aqueous saturated sodium chloride solution. After dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was subjected to silica gel column chromatography to obtain 0.055 g of 4-hydroxy-3-[3-[3-[(methoxycarbonylmethylsulfinyl)methyl]phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone [Compound No. (77a)] as a yellow crystal.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. distillationthe solvent was distilled off under reduced pressure, water
  4. additionwas added to the residue
  5. extractionthis was extracted with ethyl acetate
  6. washwashed with an aqueous sodium bicarbonate solution
  7. washfurther washed with an aqueous saturated sodium chloride solution
  8. dry with materialAfter dried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-6b59660a356f4807bafe76573ba5e6d9
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

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