Potassium Carbonate → 1-(3,5-Dimethylisoxazol-4-yl)ethanone

HRID 633699Notes

Reaction equation

HRID 633699 reaction equation
CON(C)[C:4]([C:6]1[C:7]([CH3:12])=[N:8][O:9][C:10]=1[CH3:11])=[O:5].[CH3:14][Mg]Br.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CCOCC.Cl>[CH3:12][C:7]1[C:6]([C:4](=[O:5])[CH3:14])=[C:10]([CH3:11])[O:9][N:8]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 51109753N-methoxy-N,3,5-trimethylisoxazole-4-carboxamideHCID 178418573HCID 178418573, compound

Product 1

HCID 127203171-(3,5-Dimethylisoxazol-4-yl)ethanoneYield 95.8%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 580 mg (3.15 mmol) of N-methoxy-N-methyl-3,5-dimethylisoxazole-4-carboxamide in 20 mL of THF is cooled to 0° C. A solution of 1.57 mL (4.72 mmol) of 3 M methylmagnesium bromide in ether is added. After stirring for 4 hours at room temperature, the reaction medium is taken up in 10 mL of 1 N HCl and stirred for a further 1 hour at room temperature. The mixture is then basified with K2CO3 and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and evaporated to dryness to give 420 mg of 1-(3,5-dimethylisoxazol-4-yl)ethanone, corresponding to the following characteristics:

Workup

  1. stirringstirred for a further 1 hour at room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-8e9ceea2e4da4b729bd96663af6f722c
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

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