Acrylic Acid → HCID 131734706, 화합물

HRID 1773127노트

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HRID 1773127 반응식
[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]

참가 물질

7

반응물 4

HCID 6581Acrylic AcidHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 89690163HCID 89690163, 화합물

생성물 1

HCID 131734706HCID 131734706, 화합물수율 58.8%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매

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온도
67.5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5390f510b97446bf9fdb0bed01d6f9b5
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09255071B2

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