Ethyl cyanoacetate → Ethyl 3-(4-bromophenyl)-2-cyanoprop-2-enoate

HRID 1617502

反応式

HRID 1617502 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:11].N1CCCCC1>C1(C)C=CC=CC=1>[CH2:16]([O:15][C:13](=[O:14])[C:12]([C:10]#[N:11])=[CH:6][C:5]1[CH:8]=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=1)[CH3:17]

参加物

5

反応物 3

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 707414-Bromobenzaldehyde

生成物 1

HCID 367501Ethyl 3-(4-bromophenyl)-2-cyanoprop-2-enoate収率 90%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 4-bromo-benzaldehyde (5 g) and ethyl cyanoacetate (2.9 mL) in toluene (50 mL) was added piperidine (0.046 mL), and the mixture was stirred at reflux for 2 h with a Dean-Stark separator. The mixture was cooled to rt, stirred overnight and toluene was evaporated in vacuo. The crude residue was crystallized from EtOAc to yield the title compound (6.77 g, 90%) as a light yellow solid, MS (EI): m/z=279 ([M]+, 1Br).

後処理

  1. temperatureat reflux for 2 h with a Dean-Stark separator
  2. stirringstirred overnight
  3. customtoluene was evaporated in vacuo
  4. customThe crude residue was crystallized from EtOAc

出典と根拠

ORDレコード
ord-27d9c19a64fc45d4872476ab5d8e54cc
出典データセット
uspto-grants-2014_07
特許番号
US08765730B2

関連ノート

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