Acetone → 7-Methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylthiochroman-4-one

HRID 1859339Notes

Reaction equation

HRID 1859339 reaction equation
C[C:2](C)=[O:3].[OH:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10](=[O:24])[C:11]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)([CH3:16])[CH2:12][S:13]2)=[CH:8][CH:7]=1.[C:25](=O)([O-])[O-].[K+].[K+].[CH3:31][O:32][CH2:33]Cl>O>[CH3:31][O:32][CH2:33][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10](=[O:24])[C:11]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:25][O:3][CH3:2])=[CH:19][CH:18]=3)([CH3:16])[CH2:12][S:13]2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 22033294HCID 22033294, compound

Product 1

HCID 220332467-Methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylthiochroman-4-oneYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To dry acetone solution (100 ml) of 7-hydroxy-3-(4-hydroxyphenyl)-3-methylthiochroman-4-one (2.30 g, 8.04 mmol) were added potassium carbonate (8.87 g, 64.3 mmol) and methoxymethyl chloride (4.64 ml, 61.5 mmol), and the mixture was heated under refluxing for 40 hours. After adding water, the reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate and then distilled under reduced pressure to remove the solvent. The crude product thus obtained was purified with silica gel column chromatography (ethyl acetate:hexane=1:3) to obtain 2.65 g (yield: 88%) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder refluxing for 40 hours
  3. extractionthe reaction solution was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe crude product thus obtained
  9. customwas purified with silica gel column chromatography (ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-63e273ff366f476faa546b9ffcda0c6a
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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