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

HRID 2288060ノート

反応式

HRID 2288060 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e892c006547f43a9b921d7adfb79c264
出典データセット
uspto-grants-2000_07
特許番号
US06087336

反応ノート

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