ChemicalBook CAS DataBase List 3-PHENYL-1-P-TOLYL-PROPYNONE

3-PHENYL-1-P-TOLYL-PROPYNONE synthesis

11synthesis methods

Product Name:3-PHENYL-1-P-TOLYL-PROPYNONE
CAS Number:20442-65-3
Molecular formula:C16H12O
Molecular Weight:220.27

874-60-2 Synthesis

874-60-2
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536-74-3 Synthesis

536-74-3
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20442-65-3
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Yield:20442-65-3 99%

Reaction Conditions:

Stage #1: 4-methyl-benzoyl chloridewith bis-triphenylphosphine-palladium(II) chloride;triethylamine in tetrahydrofuran at 20; for 0.166667 h;Inert atmosphere;
Stage #2: with copper(l) iodide in tetrahydrofuran at 20; for 0.166667 h;Inert atmosphere;
Stage #3: phenylacetylene in tetrahydrofuran at 20; for 6.25 h;Inert atmosphere;

Steps:

General Procedure for the synthesis of α,β-alkynicketones 6a-h (Table 1).

General procedure: A mixture of the corresponding aryloyl/alkanoyl chloride (3.0 mmol), PdCl₂(PPh₃)₂(0.05 mmol) and Et₃N (3.0 mmol) in anhydrous THF (7.5 mL) were stirred for 10 min at room temperature under argon. CuI (0.1 mmol) was then added and the reaction mixture was stirred for another 10 min. After the addition of the appropriate terminal alkyne (2.5 mmol) over 15 min, the resulting mixture was stirred at room temperature for approximately 6 h. (Note that the progress of the reaction was monitored by routine TLC for the disappearance of alkyne). After the reaction was over, ethyl acetate (50 mL) was added, and the resulting solution was washed with 0.1 N HCl (10 mL) and subsequently with a saturated NH₄Cl solution (10 mL) in a separatory funnel. After the layers were separated, organic phase was dried over MgSO₄ and evaporated on a rotary evaporator to give the crude product, which was purified by flash chromatography on silica gel using hexane/ethyl acetate (19:1) as the eluent to afford the corresponding α,β-alkynic ketone 6a-h.

References:

Karabiyikoglu, Sedef;Kelgokmen, Yilmaz;Zora, Metin [Tetrahedron,2015,vol. 71,# 25,p. 4324 - 4333] Location in patent:supporting information