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

HRID 2173423ノート

反応式

HRID 2173423 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a9e24c2718a8457990e0e319271772a3
出典データセット
uspto-grants-2015_06
特許番号
US09056859B2

反応ノート

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