m-Chloroperbenzoic acid → 3-methyl-6-(oxiran-2-yl)-3,4-dihydro-1H-isochromen-1-one

HRID 2173423노트

반응식

HRID 2173423 반응식
[CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[O:8][CH:7]([CH3:14])[CH2:6]2)=[CH2:2].C1C=C(Cl)C=C(C(OO)=[O:23])C=1>C(Cl)Cl.O>[CH3:14][CH:7]1[CH2:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([CH:1]3[CH2:2][O:23]3)[CH:4]=2)[C:9](=[O:13])[O:8]1

참가 물질

5

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 675177156-ethenyl-3-methyl-3,4-dihydro-1H-isochromen-1-one

생성물 1

HCID 772306793-methyl-6-(oxiran-2-yl)-3,4-dihydro-1H-isochromen-1-one

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

A solution of 6-ethenyl-3-methyl-3,4-dihydro-1H-isochromen-1-one (1.69 g, 8.98 mmol) in DCM (60 mL) was treated with m-CPBA (3.10 g, 17.96 mmol) overnight at room temperature. The reaction was then diluted with water (50 mL) and DCM (50 mL). The organic layer was further washed successively with saturated aqueous sodium bicarbonate (30 mL), water (30 mL), and brine (30 mL). The organic layer was then dried over magnesium sulfate, filtered and concentrated. The residue was purified via MPLC (15-40% EtOAc/Hex) to give 3-methyl-6-(oxiran-2-yl)-3,4-dihydro-1H-isochromen-1-one.

후처리

  1. washThe organic layer was further washed successively with saturated aqueous sodium bicarbonate (30 mL), water (30 mL), and brine (30 mL)
  2. dry with materialThe organic layer was then dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified via MPLC (15-40% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-a9e24c2718a8457990e0e319271772a3
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056859B2

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