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

HRID 1617502

반응식

HRID 1617502 반응식
[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]

참가 물질

5

반응물 3

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 707414-Bromobenzaldehyde

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-27d9c19a64fc45d4872476ab5d8e54cc
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765730B2

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