Acetic Acid → HCID 22087242, compound

HRID 2075560Notes

Reaction equation

HRID 2075560 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.[OH-:10].[Na+].CC(O)=[O:14]>>[CH3:9][S:8]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=1)=[O:14].[CH3:9][S:8]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=1)(=[O:14])=[O:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 3117595-Methyl-2-(methylthio)pyridine

Product 2

HCID 22087242HCID 22087242, compoundHCID 234370392-(Methanesulfonyl)-5-methylpyridine

Procedure

To a solution of 0.69 g 5-methyl-2-methylsulfanyl-pyridine in 15 mL HOAc was added NaBO3.4H2O (1.92 g). This mixture was stirred at room temperature for 5 hours. The reaction mixture was then poured into ice. NaOH (10 M) was used to adjust the pH to 7. The mixture was extracted with ethyl acetate. The organic phase was dried over sodium sulphate and concentrated in vacuo. The residue was purified by flash chromatography (silica, heptane/ethyl acetate) to yield 0.51 g of 2-methanesulfinyl-5-methyl-pyridine and 0.27 g of 2-methanesulfonyl-5-methyl-pyridine.

Workup

  1. additionThe reaction mixture was then poured into ice
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (silica, heptane/ethyl acetate)

Sources & evidence

ORD record
ord-1f135f6ff04948ddbbd5f57238d0ac6c
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

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