Acrylic Acid → HCID 131734706、化合物

HRID 1773127ノート

反応式

HRID 1773127 の反応式
[C:1]([O:4][C:5]1[CH:12]=[CH:11][C:10](I)=[CH:9][C:6]=1[CH:7]=[O:8])(=[O:3])[CH3:2].C(N(CC)CC)C.[C:21]([OH:25])(=[O:24])[CH:22]=[CH2:23].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:7]([C:6]1[CH:9]=[C:10]([CH:11]=[CH:12][C:5]=1[O:4][C:1](=[O:3])[CH3:2])[CH:23]=[CH:22][C:21]([OH:25])=[O:24])=[O:8]

参加物

7

反応物 4

HCID 6581Acrylic AcidHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 89690163HCID 89690163、化合物

生成物 1

HCID 131734706HCID 131734706、化合物収率 58.8%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6342Acetonitrile溶媒

反応条件

温度
67.5 °C

実験手順

2-Acetyloxy-5-iodobenzaldehyde (0.2 g, 0.69 mmol) is dissolved in 25 ml of acetonitrile and oxygen is removed by bubbling nitrogen through the solution. Triethylamine (0.673 ml, 4.82 mmol) and acrylic acid (0.095 ml, 1.38 mmol) are added dropwise with stirring, followed by 0.016 g of tri-o-tolylphosphine (0.069 mmol) and 0.008 of palladium(II) acetate (0.047 mmol). The mixture is heated at 65-70° C. for 4 hours, volatiles are removed by distillation and the residue is purified by column chromatography on silica gel, eluting with mixtures of ethyl acetate-hexane of increasing polarity. 3-Formyl-4-acetyloxycinnamic acid (0.095 g) is obtained as a white solid.

後処理

  1. customoxygen is removed
  2. customby bubbling nitrogen through the solution
  3. customvolatiles are removed by distillation
  4. customthe residue is purified by column chromatography on silica gel
  5. washeluting with mixtures of ethyl acetate-hexane
  6. temperatureof increasing polarity

出典と根拠

ORDレコード
ord-5390f510b97446bf9fdb0bed01d6f9b5
出典データセット
uspto-grants-2016_02
特許番号
US09255071B2

反応ノート

読み込み中…