Dimethyl Sulfate → HCID 68743481, compound

HRID 505935Notes

Reaction equation

HRID 505935 reaction equation
[C:1](=O)([O-])[O-].[Na+].[Na+].S(OC)(OC)(=O)=O.[OH:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[O:18][C:17](=[O:25])[CH:16]=1>CC(C)=O>[CH3:1][O:14][C:15]1[CH:20]=[C:19]([C:21]([F:22])([F:23])[F:24])[O:18][C:17](=[O:25])[CH:16]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 10340Sodium CarbonateHCID 670000654-Hydroxy-6-(trifluoromethyl)-2H-pyran-2-one

Product 1

HCID 68743481HCID 68743481, compoundYield 107.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Sodium carbonate (1.35 g, 13 mmol) and dimethyl sulfate (2.17 g, 17 mmol) were added to a solution of 4-hydroxy-6-trifluoromethylpyran-2-one (3.0 g, 17 mmol) in acetone (50 mL). The mixture was heated under reflux for 3 hours and, after cooling, filtered. Concentration of the filtrate resulted in 2.9 g of crude product as a brown oil. It was possible to obtain 4-methoxy-6-trifluoromethylpyran-2-one (2.74 g, 14 mmol, 83%) as colorless needles with a melting point of 61° C. by crystallization from hexane.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureafter cooling
  4. filtrationfiltered
  5. customConcentration of the filtrate resulted in 2.9 g of crude product as a brown oil

Sources & evidence

ORD record
ord-13b96b5424b94840b3dad0ecf7d5d57a
Source dataset
uspto-grants-2010_08
Patent number
US07781601B2

Reaction notes

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