Water → 2-m-Tolyl-isoxazolidin-3-one

HRID 1754986노트

반응식

HRID 1754986 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-5e16d19ca812468888c7a3f5f854e856
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169254B2

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