Tetrahydrofuran → 1-(1-Ethylpropyl)-5-methyl-3-(methylsulfonyl)-2(1H)-pyrazinone

HRID 1271140Notes

Reaction equation

HRID 1271140 reaction equation
[CH2:1]([CH:3]([N:6]1[CH:11]=[C:10]([CH3:12])[N:9]=[C:8](SC)[C:7]1=[O:15])[CH2:4][CH3:5])[CH3:2].O[O:17][S:18]([O-:20])=O.[K+].[CH2:22]1COCC1>O.C(OCC)(=O)C>[CH2:1]([CH:3]([N:6]1[CH:11]=[C:10]([CH3:12])[N:9]=[C:8]([S:18]([CH3:22])(=[O:20])=[O:17])[C:7]1=[O:15])[CH2:4][CH3:5])[CH3:2]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 588451711-(1-Ethylpropyl)-5-methyl-3-(methylthio)-2 (1H)-pyrazinone

Product 1

HCID 588451731-(1-Ethylpropyl)-5-methyl-3-(methylsulfonyl)-2(1H)-pyrazinoneYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A solution of XXXII (200 mg, 0.9 mmol) in THF (25 mL) was treated with Oxone™ (1.1 g, 1.8 mmol) portionwise as a solid at 25° C. The reaction mixture was stirred at 25° C. for 16 h and diluted with water (20 mL) and ethyl acetate (25 mL). The organic phase was dried (MgSO4), filtered, and concentrated in vacuo to give the product XXXIII (153 mg, 67%) as a yellow oil.

Workup

  1. dry with materialThe organic phase was dried (MgSO4)
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4e23d85e738f427bb2cd3f2727181f6d
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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