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

HRID 2281309Notes

Reaction equation

HRID 2281309 reaction equation
[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][C@@H: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

Participants

5

Reactant 2

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

Product 1

HCID 86693039(3R)-3-methyl-6-(oxiran-2-yl)-3,4-dihydro-1H-isochromen-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 6-ethenyl-3-methyl-3,4-dihydro-1H-isochromen-1-one (1.7 g, 9.0 mmol) in DCM (60 mL) was treated with m-CPBA (3.1 g, 18 mmol) and then stirred 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 (3R)-3-methyl-6-(oxiran-2-yl)isochroman-1-one.

Workup

  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)

Sources & evidence

ORD record
ord-8859591d32cb4f46966073ad3c3a7060
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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