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

HRID 2209663Notes

Reaction equation

HRID 2209663 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 saturated salt water and dried over sodium sulfate anhydride. 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 saturated salt water
  6. dry with materialdried over sodium sulfate anhydride
  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-cca43a091fdd45e7b88a5eea6e00dfcf
Source dataset
uspto-grants-1995_10
Patent number
US05455267

Reaction notes

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