Methanol → HCID 15457191, compound

HRID 992886Notes

Reaction equation

HRID 992886 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][C:8]([CH:11]([S:14][CH3:15])[CH2:12][CH3:13])=[CH:7][C:6]=2[C:5]([C:16]2[C:17](=[O:27])[N:18]([CH3:26])[C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:21]=2)=[C:4]([F:28])[CH:3]=1.[OH2:29].OOS([O-])=O.[K+].C[OH:37]>>[Cl:1][C:2]1[C:10]2[O:9][C:8]([CH:11]([S:14]([CH3:15])(=[O:37])=[O:29])[CH2:12][CH3:13])=[CH:7][C:6]=2[C:5]([C:16]2[C:17](=[O:27])[N:18]([CH3:26])[C:19]([C:22]([F:24])([F:23])[F:25])=[CH:20][CH:21]=2)=[C:4]([F:28])[CH:3]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 15457190HCID 15457190, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 15457191HCID 15457191, compoundYield 85%

Procedure

0.20 g (0.461 mmol) of 3-[7-chloro-5-fluoro-2-(1-methylthiopropyl)benzofuran-4-yl]-1-methyl-6-trifluoromethyl-2-(1H)-pyridone was dissolved in 15 ml of methanol, and 5 ml of water and 0.57 g (0.922 mmol) of Oxone were added thereto, followed by stirring at room temperature for 2 hours. Insoluble substances were removed by filtration. Then, methanol was distilled off under reduced pressure, and the obtained residue was poured into water and extracted with ethyl acetate. After washing with water, the organic layer was dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.18 g (yield: 85%) of the desired product. Melting point: 146-148° C.

Workup

  1. customInsoluble substances were removed by filtration
  2. distillationThen, methanol was distilled off under reduced pressure
  3. additionthe obtained residue was poured into water
  4. extractionextracted with ethyl acetate
  5. washAfter washing with water
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. distillationEthyl acetate was distilled off under reduced pressure
  8. customThen, the obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-22316923dde14bacad0a6bde5e8c484f
Source dataset
uspto-grants-2002_10
Patent number
US06472348B1

Reaction notes

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