Potassium Carbonate → HCID 86679290, compound

HRID 1519731Notes

Reaction equation

HRID 1519731 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[CH3:37][O:38][C:39](=[O:51])[C:40]1[CH:45]=[CH:44][C:43]([C:46]#[C:47]/[CH:48]=[CH:49]/Cl)=[CH:42][CH:41]=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>[CH3:37][O:38][C:39](=[O:51])[C:40]1[CH:45]=[CH:44][C:43]([C:46]#[C:47]/[CH:48]=[CH:49]/[C:6]2[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=2)=[CH:42][CH:41]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 5910734-Formylphenylboronic AcidHCID 59417216HCID 59417216, compound

Product 1

HCID 86679290HCID 86679290, compoundYield 69%

Reagents, catalysts & solvents 4

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

Procedure

4-Formylphenylboronic acid (0.49 g), PdCl2(PPh3)2 (0.11 g), triphenylphosphine (78 mg) and potassium carbonate (0.82 g) were added to a toluene (3.5 mL)-ethanol (1.8 mL) solution of 4-((E)-4-chlorobut-3-en-1-yn-1-yl)benzoic acid methyl ester (0.70 g) as obtained by the method described in the patent (WO2008/154642), 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 and IPA were 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-[(E)-4-(4-formylphenyl)but-3-en-1-yn-1-yl)benzoic acid methyl ester (orange solid) (0.59 g, 69%).

Workup

  1. customas obtained by the method
  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 and IPA were 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-33d3472e3e6c45cb9025ccb20942b9a2
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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