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

HRID 1802323노트

반응식

HRID 1802323 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
55 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b1c43041b0794deda4cc88c6e014edc5
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349870B2

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