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

HRID 2173423Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2173423
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-a9e24c2718a8457990e0e319271772a3
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09056859B2

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