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

HRID 333326

反応式

HRID 333326 の反応式
[C:1]([CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])#[N:2].[Cl:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH:15]=O.N1CCCCC1>CCO>[C:1](/[C:3](=[CH:15]\[C:14]1[CH:17]=[CH:18][C:19]([Cl:20])=[C:12]([Cl:11])[CH:13]=1)/[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])#[N:2]

参加物

5

反応物 3

HCID 8082PiperidineHCID 227103,4-DichlorobenzaldehydeHCID 70693tert-Butyl cyanoacetate

生成物 1

HCID 68751356(E)-tert-butyl 2-cyano-3-(3,4-dichlorophenyl)acrylate収率 81.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

A solution of tert-butyl cyanoacetate (2.52 ml, 17.63 mmol), 3,4-dichlorobenzaldehyde (2.57 g, 14.69 mmol) and piperidine (0.145 ml, 1.469 mmol) in EtOH (50 ml) was allowed to stir at 80° C. for 15 hours, and then cooled to ambient temperature. A half volume of the solvent was evaporated, and 400 ml of water was added to the resulting mixture. The precipitated solid was collected and washed with 5% iPrOH/H2O (200 ml). The solid was dried under reduced pressure to give (E)-tert-butyl 2-cyano-3-(3,4-dichlorophenyl)acrylate (3.577 g); Retention time=1.61 minutes (condition A); MS (ES+)=315.1 (m+18).

後処理

  1. temperaturecooled to ambient temperature
  2. customA half volume of the solvent was evaporated
  3. addition400 ml of water was added to the resulting mixture
  4. customThe precipitated solid was collected
  5. washwashed with 5% iPrOH/H2O (200 ml)
  6. customThe solid was dried under reduced pressure

出典と根拠

ORDレコード
ord-1491605790b04672bdfb6bed058d5069
出典データセット
uspto-grants-2014_11
特許番号
US08877815B2

関連ノート

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