Methyl iodide → 7-Isopropoxy-5-methoxy-2-methylthiochromone

HRID 1779525Notes

Reaction equation

HRID 1779525 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[S:14])[CH:5]=[C:6]([CH3:13])[O:7]2.C(=O)([O-])[O-].[K+].[K+].[CH:21](I)([CH3:23])[CH3:22].[CH3:25]I>O.CC(C)=O>[CH:21]([O:12][C:10]1[CH:9]=[C:8]2[C:3]([C:4](=[S:14])[CH:5]=[C:6]([CH3:13])[O:7]2)=[C:2]([O:1][CH3:25])[CH:11]=1)([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 1361024115,7-Dihydroxy-2-methylthiochromone

Product 1

HCID 570102217-Isopropoxy-5-methoxy-2-methylthiochromoneYield 54.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A mixture consisting of 354 mg (1.58 mmol) of 5,7-dihydroxy-2-methylthiochromone, 1.09 g (7.90 mmol) potassium carbonate, 0.79 ml (7.90 mmol) isopropyl iodide, and 20 ml acetone was refluxed overnight. Then, 2.95 ml (47.4 mmol) methyl iodide was added, and the mixture was further refluxed overnight. Water was added to the solution thus reacted. The product was extracted twice with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was distilled out under reduced pressure. The resulting crude product was purified by flash column chromatography (hexane:ethyl acetate=1:3-1:6), whereby 228 mg of 7-isopropoxy-5-methoxy-2-methylthiochromone was obtained (yield: 52%).

Workup

  1. temperaturewas refluxed overnight
  2. temperaturethe mixture was further refluxed overnight
  3. customthus reacted
  4. extractionThe product was extracted twice with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled out under reduced pressure
  8. customThe resulting crude product was purified by flash column chromatography (hexane:ethyl acetate=1:3-1:6)

Sources & evidence

ORD record
ord-74da53e7ff204e638b57b4ca3c574581
Source dataset
uspto-grants-1997_05
Patent number
US05627204

Reaction notes

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