Potassium Carbonate → HCID 86679287, compound

HRID 1519728Notes

Reaction equation

HRID 1519728 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)=[O:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].Cl/[CH:40]=[CH:41]/[C:42]#[C:43][C:44]1[CH:51]=[CH:50][C:47]([CH:48]=[O:49])=[CH:46][CH:45]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C.C(O)C.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:10]=[CH:9][C:8](/[CH:40]=[CH:41]/[C:42]#[C:43][C:44]2[CH:45]=[CH:46][C:47]([CH:48]=[O:49])=[CH:50][CH:51]=2)=[CH:7][CH:6]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27343694-Methoxycarbonylphenylboronic acidHCID 86679286HCID 86679286, compound

Product 1

HCID 86679287HCID 86679287, compoundYield 81.2%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Methoxycarbonylphenylboronic acid (1.0 g), PdCl2(PPh3)2 (0.18 g), triphenylphosphine (0.13 g) and potassium carbonate (1.4 g) were added to a toluene (5.0 mL)-ethanol (2.5 mL) solution of 4-((E)-4-chlorobut-3-en-1-yn-1-yl)benzaldehyde (0.97 g) as obtained in Example 22-(1), and the mixture was heated and refluxed for 3 hours in a nitrogen atmosphere. After the reaction mixture was cooled to room temperature, ethyl acetate was added, the insolubles were filtered out, and the filtrate was concentrated under reduced pressure. IPE was added to the resulting residue, and the solids were filtered out, whereafter chloroform and OH type silica gel (10 g) were added. The insolubles were filtered out, and the filtrate was concentrated under reduced pressure to obtain 4-[(1E)-4-(4-formylphenyl)but-1-en-3-yn-1-yl]benzoic acid methyl ester (light brown solid) (1.2 g, 78%).

Workup

  1. customas obtained in Example 22-(1)
  2. temperaturethe mixture was heated
  3. temperaturerefluxed for 3 hours in a nitrogen atmosphere
  4. filtrationthe insolubles were filtered out
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionIPE was added to the resulting residue
  7. filtrationthe solids were filtered out, whereafter chloroform and OH type silica gel (10 g)
  8. additionwere added
  9. filtrationThe insolubles were filtered out
  10. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1bc53b09b6084d8faebcb76d833eaef1
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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