Acetone → HCID 14855466, compound

HRID 477390Notes

Reaction equation

HRID 477390 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[C:7]([CH3:8])=[C:6]([OH:9])[O:5][N:4]=1.CC(C)=O.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][C:24]([O:26][CH3:27])=[O:25]>O>[F:11][C:2]([F:1])([F:10])[C:3]1[C:7]([CH3:8])=[C:6]([O:9][CH2:23][C:24]([O:26][CH3:27])=[O:25])[O:5][N:4]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 178427875HCID 178427875, compound

Product 1

HCID 14855466HCID 14855466, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1.00 g (6 mmole) of 3-trifluoromethyl-4-methyl-5-hydroxyisoxazole were added 10 ml of dry acetone and 1.00 g (7.2 mmole) of anhydrous potassium carbonate and the resulting mixture was stirred at room temperature for one hour. After addition of methyl bromoacetate (1.10 g, 7.2 mmole), the mixture was refluxed for 30 hours. The reaction mixture was mixed with water (100 ml) and, extracted with diethyl ether. The diethyl ether phase was dried with anhydrous magnesium sulfate, evaporated under reduced pressure, and the residue was purified by chromatography on silica gel to give 0.73 g of the title compound as colorless viscous liquid, yield 53.6%.

Workup

  1. temperaturethe mixture was refluxed for 30 hours
  2. extractionextracted with diethyl ether
  3. dry with materialThe diethyl ether phase was dried with anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-df55ac03830941539eea6c84d9d08ab2
Source dataset
uspto-grants-1989_12
Patent number
US04888044

Reaction notes

Loading…