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ChemicalBook CAS DataBase List Phenylpropiolic acid
637-44-5

Phenylpropiolic acid synthesis

11synthesis methods
Add phenylacetylene 6 mmol and ultra-dry tetrahydrofuran 25-30 mL in a 100 mL reaction flask, followed by evacuation treatment, N2 protection, put the reaction flask into an ethanol solution at -78°C, and then continue to add n-butyllithium 6 mmol, and af
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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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