Methanol → 7-Isopropoxy-5-methoxy-2-methylsulfinylchromone

HRID 441060Notes

Reaction equation

HRID 441060 reaction equation
OO[S:3]([O-:5])=O.[K+].[CH:7]([O:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15](=S)[CH:16]=[C:17](C)[O:18]2)=[C:13]([O:23][CH3:24])[CH:12]=1)([CH3:9])[CH3:8].[OH2:25].[CH3:26]O>>[CH:7]([O:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15](=[O:25])[CH:16]=[C:17]([S:3]([CH3:26])=[O:5])[O:18]2)=[C:13]([O:23][CH3:24])[CH:12]=1)([CH3:9])[CH3:8]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 570102217-Isopropoxy-5-methoxy-2-methylthiochromone

Product 1

HCID 229064677-Isopropoxy-5-methoxy-2-methylsulfinylchromone

Procedure

2 ml aqueous solution of 347 mg oxone (0.564 mmol) was added dropwise to 4 ml of 158 mg of 7-isopropoxy-5-methoxy-2-methylthiochromone (0.564 mmol) in methanol, and the mixture was stirred for 30 min. After addition of water, the reaction solution was extracted twice with ethyl acetate, and the organic layer washed with saturated NaCl water and dried over sodium sulfate anhydride. The solvent was then distilled off under reduced pressure, thus giving 147 mg of 7-isopropoxy-5-methoxy-2-methylsulfinylchromone (containing a little sulfone). This product was subjected without purification to the following reaction.

Workup

  1. extractionthe reaction solution was extracted twice with ethyl acetate
  2. washthe organic layer washed with saturated NaCl water
  3. dry with materialdried over sodium sulfate anhydride
  4. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-ed02e5a589b74be5a271bdb0ca9296ed
Source dataset
uspto-grants-1996_05
Patent number
US05521216

Reaction notes

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