Benzoyl Peroxide → 6-Methoxyisochromen-1-one

HRID 69488ノート

反応式

HRID 69488 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[O:8][CH2:7][CH2:6]2.C1C(=O)N(Br)C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClC(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[O:8][CH:7]=[CH:6]2

参加物

5

反応物 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 124011826-Methoxy-3,4-dihydro-1H-2-benzopyran-1-one

生成物 1

HCID 151110126-Methoxyisochromen-1-one

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

A solution of 6-methoxy-isochroman-1-one (15.1 g), NBS (27 g) and benzoyl peroxide (500 mg) in tetrachloromethane (250 mL) was heated for 3 h under reflux, while irradiated with light. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in triethylamine (100 mL) and stirred for 48 h at room temperature. The reaction mixture was distributed between water and ethyl acetate and was adjusted to pH 1 with concentrated hydrochloric acid. The organic phase was separated, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel. In this way the product was obtained with molecular weight 176.17 (C10H8O3); MS (ESI): 177 (M+H+).

後処理

  1. temperatureunder reflux
  2. customwhile irradiated with light
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved in triethylamine (100 mL)
  6. customThe organic phase was separated
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was chromatographed on silica gel
  10. customIn this way the product was obtained with molecular weight 176.17 (C10H8O3)

出典と根拠

ORDレコード
ord-e034ded2ebdd4e6782c6ba52a709cceb
出典データセット
uspto-grants-2014_09
特許番号
US08822495B2

反応ノート

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