ChemicalBook CAS DataBase List Phenylpropiolic acid

Phenylpropiolic acid synthesis

11synthesis methods

Product Name:Phenylpropiolic acid
CAS Number:637-44-5
Molecular formula:C9H6O2
Molecular Weight:146.14

591-50-4 Synthesis

591-50-4
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$10.00/1g

471-25-0
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637-44-5
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$6.00/1g

Yield:637-44-5 96%

Reaction Conditions:

with bis-triphenylphosphine-palladium(II) chloride;1,8-diazabicyclo[5.4.0]undec-7-ene;1,4-di(diphenylphosphino)-butane in dimethyl sulfoxide at 50; for 5 h;Sealed flask;Sonogashira coupling;

Steps:

21. Typical experimental procedure:
General procedure: Method A; Pd(PPh₃)₂Cl₂ (35.1 mg, 0.05 mmol), 1,4-bis(diphenylphosphino)butane (42.6 mg, 0.1 mmol), aryl halides (2.0 mmol), and DBU (1.52 g, 10.0 mmol) were combined with DMSO (4.0 mL), in a small round-bottomed flask. Propiolic acid (1a) (140.0 mg, 2.0 mmol) was added, and the flask was sealed with a septum. The resulting mixture was placed in an oil bath at 50 °C for 5 h. The reaction was poured into Ethyl acetate and extracted with water saturated by NaHCO₃. The aqueous layer was acidified to pH 2.0 by cold 1 N HCl(aq) and extracted with CH₂Cl₂. The organic layer dried over MgSO₄, and filtered. The solvent was removed under vacuum, and the resulting crude product was purified by flash chromatography on silica gel to give 3a (208.6 mg, 96% yield). The spectroscopic data of 3a-j are as follows.

References:

Park, Kyungho;Palani, Thiruvengadam;Pyo, Ayoung;Lee, Sunwoo [Tetrahedron Letters,2012,vol. 53,# 7,p. 733 - 737] Location in patent:experimental part

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