Hydrogen Peroxide → HCID 54186441, compound

HRID 1418550Notes

Reaction equation

HRID 1418550 reaction equation
[OH:1]O.[CH2:3]([S:5][C:6]([CH2:11][CH3:12])=[CH:7][N+:8]([O-:10])=[O:9])[CH3:4]>C(O)=O>[CH2:3]([S:5]([C:6]([CH2:11][CH3:12])=[CH:7][N+:8]([O-:10])=[O:9])=[O:1])[CH3:4]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 53642910HCID 53642910, compound

Product 1

HCID 54186441HCID 54186441, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

2-Ethylsulfinyl-1-nitrobutene was prepared by the dropwise addition of aqueous hydrogen peroxide (1.05 g., 0.0093 mol) to a stirred solution of 2-ethylthio-1-nitrobutene (1.50 g., 0.0093 mol) in formic acid (20 ml.). The resulting solution was stirred at room temperature for 18 hours. The solvent was removed under reduced pressure and the residue was dissolved in methylene chloride, washed successively with saturated aqueous sodium bicarbonate (1×50 ml.) and deionized water (1×50 ml.), dried over anhydrous magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (2:1 hexanes/ethyl acetate) afforded the isomeric mixture of the product as a yellow oil, 0.42g., 25% yield. 1H-NMR (CDCl3): δ 1.26, m, 3H, CH3 ; 1.5, t, 3H, CH3 ; 2.5-2.85, m, 2H, --CH2 --; 2.85-3.2, m, 2H, SCH2 --; 7.2+7.3, 2s, 1H, olefinic H.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in methylene chloride
  3. washwashed successively with saturated aqueous sodium bicarbonate (1×50 ml.) and deionized water (1×50 ml.)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (2:1 hexanes/ethyl acetate)
  8. customafforded

Sources & evidence

ORD record
ord-147e069b3c6d4a63a8cef85e83d767a6
Source dataset
uspto-grants-1999_03
Patent number
US05883134

Reaction notes

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