o-Fluorostyrene → 2-Chloro-1-[4,5-dihydro-5-(2-fluorophenyl)-3-isoxazolyl]ethanone

HRID 1802323ノート

反応式

HRID 1802323 の反応式
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[CH2:5].C(=O)(O)[O-].[Na+].[Cl:15][CH2:16][C:17](=[O:22])[C:18](Cl)=[N:19][OH:20]>C1(C)C=CC=CC=1>[Cl:15][CH2:16][C:17]([C:18]1[CH2:5][CH:4]([C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[F:1])[O:20][N:19]=1)=[O:22]

参加物

5

反応物 3

HCID 123056o-FluorostyreneHCID 516892Sodium BicarbonateHCID 68330913-chloro-N-hydroxy-2-oxopropanimidoyl chloride

生成物 1

HCID 866476752-Chloro-1-[4,5-dihydro-5-(2-fluorophenyl)-3-isoxazolyl]ethanone収率 85.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
55 °C

実験手順

To a suspension of 2-fluorostyrene (2.78 g, 22.8 mmol) and sodium bicarbonate (2.88 g, 34.2 mmol) in anhydrous toluene (15 mL) heated at 55° C. was added 3-chloro-N-hydroxy-2-oxo-propanimidoyl chloride (1.78 g, 11.4 mmol). After 2 h at 55° C., the reaction mixture was cooled, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel using 10% ethyl acetate in hexanes as eluant to provide the title compound as a yellow solid (2.35 g) melting at 42-44° C.

後処理

  1. temperaturethe reaction mixture was cooled
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by column chromatography on silica gel using 10% ethyl acetate in hexanes as eluant

出典と根拠

ORDレコード
ord-b1c43041b0794deda4cc88c6e014edc5
出典データセット
uspto-grants-2013_01
特許番号
US08349870B2

反応ノート

読み込み中…