Acetic Acid → HCID 22087242, compound

HRID 2062128Notes

Reaction equation

HRID 2062128 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-52d0e69f5ebb404d9234fcd3b6ffb4ea
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

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