Water → Methyl3-(2-cyanobenzo[b]thiophen-5-yl)acrylate

HRID 2288060노트

반응식

HRID 2288060 반응식
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].C(N(CC)CC)C.[C:14]([C:16]1[S:20][C:19]2[CH:21]=[CH:22][C:23](I)=[CH:24][C:18]=2[CH:17]=1)#[N:15].O>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:6][O:5][C:1](=[O:4])[CH:2]=[CH:3][C:23]1[CH:22]=[CH:21][C:19]2[S:20][C:16]([C:14]#[N:15])=[CH:17][C:18]=2[CH:24]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 187029595-Iodobenzo[b]thiophene-2-carbonitrile

생성물 1

HCID 54151697Methyl3-(2-cyanobenzo[b]thiophen-5-yl)acrylate수율 61%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

Methyl acrylate (2 g), triethylamine (2.35 g) and palladium acetate (0.05 g) was added to 2-cyano-5-iodobenzo[b]thiophene (4.8 g) in DMF (25 ml) and the mixture was stirred under argon at 90° C. for 30 minutes. The mixture was allowed to cool and then added to water (50 ml). The solid which precipitated was collected by filtration and dissolved in chloroform. Activated charcoal was added and the mixture filtered and the filtrate dried (MgSO4). Solvent was removed by evaporation to give methyl3-(2-cyanobenzo[b]thiophen-5-yl)acrylate (2.5 g); NMR (d6 -DMSO): 3.75 (s, 3H), 6.7 (d, 1H), 7.8 (d, 1H), 8.0 (dd, 1H), 8.2 (d, 1H), 8.3 (d, 1H), 8.85 (s, 1H).

후처리

  1. temperatureto cool
  2. customThe solid which precipitated
  3. filtrationwas collected by filtration
  4. dissolutiondissolved in chloroform
  5. additionActivated charcoal was added
  6. filtrationthe mixture filtered
  7. dry with materialthe filtrate dried (MgSO4)
  8. customSolvent was removed by evaporation

출처 및 근거

ORD 기록
ord-e892c006547f43a9b921d7adfb79c264
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06087336

반응 노트

불러오는 중…