(E)-tert-butyl 2-cyano-3-(3,4-dichlorophenyl)acrylate → Tert-butyl 2-cyano-3-(3,4-dichlorophenyl)propanoate

HRID 333325노트

반응식

HRID 333325 반응식
[C:1](/[C:3](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)/[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])#[N:2]>CC(O)=O.C1(C)C=CC=CC=1.[Cl-].[Na+].O.[Zn]>[C:1]([CH:3]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=1)[C:4]([O:6][C:7]([CH3:9])([CH3:8])[CH3:10])=[O:5])#[N:2]

참가 물질

6

반응물 1

HCID 68751356(E)-tert-butyl 2-cyano-3-(3,4-dichlorophenyl)acrylate

생성물 1

HCID 68748010Tert-butyl 2-cyano-3-(3,4-dichlorophenyl)propanoate수율 77.5%

시약·촉매·용매 4

HCID 23994Zinc촉매HCID 176Acetic Acid용매HCID 1140Toluene용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
100 °C

실험 절차

A suspension of (E)-tert-butyl 2-cyano-3-(3,4-dichlorophenyl)acrylate (1.05 g, 3.52 mmol) and zinc (3.45 g, 52.8 mmol) in AcOH (20 ml) was allowed to stir at 100° C. After stirred for 1 hour, the reaction mixture was cooled to ambient temperature, and diluted with toluene and brine. The phases were separated, and the organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give tert-butyl 2-cyano-3-(3,4-dichlorophenyl)propanoate (819 mg); Retention time=1.41 minutes (condition B); MS (ES+)=317.0 (m+18).

후처리

  1. stirringAfter stirred for 1 hour
  2. temperaturethe reaction mixture was cooled to ambient temperature
  3. customThe phases were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-4ac60e95d9b7405da0326c6a5336e5f7
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877815B2

반응 노트

불러오는 중…