Dimethyl Sulfate → 4-Fluoro-7-methoxy-2,3-dihydro-1H-inden-1-one

HRID 1492955Notes

Reaction equation

HRID 1492955 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]2[C:9]=1[CH2:10][CH2:11][C:12]2=[O:18].S(OC)(OC)(=O)=O>CC(C)=O>[F:7][C:8]1[CH:16]=[CH:15][C:14]([O:17][CH3:1])=[C:13]2[C:9]=1[CH2:10][CH2:11][C:12]2=[O:18]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 152684884-Fluoro-7-hydroxy-2,3-dihydro-1H-inden-1-one

Product 1

HCID 146450284-Fluoro-7-methoxy-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a nitrogen atmosphere, to 300 g powdered potassium carbonate in 1.5 1 of acetone is added 121 g II under stirring, followed by 83 ml of dimethyl sulphate. After heating to reflux for 2 hrs, the solvent is distilled off, water is added and the mixture refluxed for a further hour. Extraction with methylene chloride and evaporation gives 125 g of crude III, which is purified by crystallization from EtOAc, m.p. 118°-120°.

Workup

  1. temperatureAfter heating
  2. temperatureto reflux for 2 hrs
  3. distillationthe solvent is distilled off
  4. additionwater is added
  5. temperaturethe mixture refluxed for a further hour
  6. extractionExtraction
  7. customwith methylene chloride and evaporation

Sources & evidence

ORD record
ord-648bc41352814c19b6de55e09197bcdd
Source dataset
uspto-grants-1994_12
Patent number
US05376687

Reaction notes

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