m-Chloroperbenzoic acid → Methyl 2-phenyloxirane-2-carboxylate

HRID 1099016ノート

反応式

HRID 1099016 の反応式
[CH3:1][O:2][C:3](=[O:12])[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[CH2:5].C1C=C(Cl)C=C(C(OO)=[O:21])C=1>C(Cl)Cl>[CH3:1][O:2][C:3]([C:4]1([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:5][O:21]1)=[O:12]

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 193334Methyl atropate

生成物 1

HCID 12594817Methyl 2-phenyloxirane-2-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
45 °C

実験手順

The title compound was synthesized according to a literature method (Whitman Tetrahedron 1985, 41, 1183). To a mixture of 2-phenylacrylic acid methyl ester (7.92 g, 45 mmol) in 60 ml of methylene chloride was added mCPBA (13.1 g, 58.5 mmol) and the reaction was stirred at 45° C. overnight. The reaction mixture was then filtered and the solid was washed with methylene chloride. The filtrate was washed three times with 50 ml of equal parts solution consisting of saturated Na2S2O3 and saturated NaHCO3. The organic layer was washed with water and brine, dried over MgSO4, and concentrated under reduced pressure to afford the title compound in greater than 95% purity according to 1H NMR (85% yield). 1H NMR (CDCl3, 300 MHz) δ: 7.50-7.30 (m, 5H), 4.22 (q, J=7.2 Hz, 2H), 3.40 (d, J,=7.1 Hz, 1H), 2.95 (d, J=7.1 Hz, 1H), 1.26 (t, J=7.2 Hz, 3H) ppm.

後処理

  1. customThe title compound was synthesized
  2. filtrationThe reaction mixture was then filtered
  3. washthe solid was washed with methylene chloride
  4. washThe filtrate was washed three times with 50 ml of equal parts solution
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-46764ac44eeb423e97af8d2be89458ee
出典データセット
uspto-grants-2012_03
特許番号
US08143375B2

反応ノート

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