Water → 2-m-Tolyl-isoxazolidin-3-one

HRID 1754986Notes

Reaction equation

HRID 1754986 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][OH:8])[CH:2]=1.[C:10](=[O:13])([O-])[O-].[K+].[K+].O.[C:17](OCC)(=O)[CH3:18]>CN(C)C=O>[C:1]1([CH3:9])[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[C:10](=[O:13])[CH2:18][CH2:17][O:8]2)[CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 196988Benzenamine, N-hydroxy-3-methyl-

Product 1

HCID 668172992-m-Tolyl-isoxazolidin-3-oneYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Chloro-propionyl (157 μL, 1.65 mmol) was added to a mixture of N-m-tolyl-hydroxylamine (235 mg, 1.69 mmol) and potassium carbonate (223 mg, 1.69 mmol) in N,N-dimethylformamide (1.7 mL) at −10° C. The mixture was stirred at room temperature for 2.5 hours, and water and ethyl acetate were then added. The organic layer and the aqueous layer were separated, and the aqueous layer was repeatedly extracted with ethyl acetate three times. The organic layers were combined, washed with water twice and saturated brine, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 2-m-tolyl-isoxazolidin-3-one as a pale yellow solid (213 mg, 73%).

Workup

  1. customThe organic layer and the aqueous layer were separated
  2. extractionthe aqueous layer was repeatedly extracted with ethyl acetate three times
  3. washwashed with water twice
  4. concentrationsaturated brine, and then concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5e16d19ca812468888c7a3f5f854e856
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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