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

HRID 333325ノート

反応式

HRID 333325 の反応式
[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]

参加物

6

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒HCID 1140Toluene溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4ac60e95d9b7405da0326c6a5336e5f7
出典データセット
uspto-grants-2014_11
特許番号
US08877815B2

反応ノート

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