m-Chloroperbenzoic acid → 4-fluoro-5-(oxiran-2-yl)-3H-2-benzofuran-1-one

HRID 1501837ノート

反応式

HRID 1501837 の反応式
[F:1][C:2]1[C:10]([CH:11]=[CH2:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][O:5][C:6]2=[O:13].C1C=C(Cl)C=C(C(OO)=[O:22])C=1>C(Cl)Cl>[F:1][C:2]1[C:10]([CH:11]2[CH2:12][O:22]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][O:5][C:6]2=[O:13]

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 666441764-fluoro-5-vinyl-3H-isobenzofuran-1-one

生成物 1

HCID 595686724-fluoro-5-(oxiran-2-yl)-3H-2-benzofuran-1-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 4-fluoro-5-vinyl-3H-isobenzofuran-1-one (4.0 g, 17.3 mmol) in 100 mL of DCM was slowly added mCPBA (6.0 g, 85% purity, 34.6 mmol) in 50 mL of DCM at 0° C. After warming to room temperature, the mixture was stirred overnight. The mixture was washed with aqueous Na2SO3 until KI paper didn't change color. The organic layers were washed with brine and then concentrated. The residue was purified by column chromatography to give 4-fluoro-5-oxiranyl-3H-isobenzofuran-1-one. 1H-NMR (400 MHz, CDCl3) δ ppm 7.71 (d, J=7.8 Hz, 1H), 7.37-7.40 (m, 1H), 5.37 (s, 2H), 4.21-4.22 (m, 1H), 3.25-3.27 (m, 1H), 2.80-2.82 (m, 1H).

後処理

  1. customat 0° C
  2. washThe mixture was washed with aqueous Na2SO3 until KI paper didn't change color
  3. washThe organic layers were washed with brine
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-fe0e006c1d1540c8aaf0cd24b009f88d
出典データセット
uspto-grants-2015_12
特許番号
US09206198B2

反応ノート

読み込み中…