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With PEG2(at)SiO2(at)Fe3O4; In water; for 1.25h;Reflux;
General procedure: A magnetically stirred solution of alpha-bromo ketone (1.0 mmol) andNaX (2.0 mmol) in water (5.0 mL), PEGSiO2Fe3O4 (50 mg) was added. The resulting suspension was stirred under reflux conditions for the time shown in Table 1. After completion of the reaction that confirmed by TLC, the MNPs were removed magnetically and solid was filtered off, washed with water and subjected to flash chromatography.The desired phenacyl derivatives obtained in 82% to 94% isolated yields.
74%
With 1,4-bis(imidazol-1-yl)butane-based poly(ionic liquid); In water; at 60℃; for 0.25h;Green chemistry;
General procedure: A magnetically stirred mixture of alpha-bromo ketone (1.0 mmol) with NaY (1.5 mmol) and the catalyst 3(0.01 g) in water (5 mL) was heated to 60C for the time specified in the table. Progress of the reaction was monitored by TLC. After completion of the reaction,diethyl ether (3×5 mL) was added and the obtained organic phase was separated and dried with CaCl2. The solvent was removed in vacuo. The residue formed was purified by column chromatography on silica gel to give the corresponding phenacyl derivatives.
With triethylamine; In acetonitrile; at 80℃; for 2h;
4-(Bromoacetyl)bromobenzene (6.00 g, 21.6 mmol, 1 equiv),Acetonitrile (50 mL), triethylamine (6.0 mL, 43.2 mmol, 2 equiv),Acetic acid (2.5 mL, 43.2 mmol, 2 equiv) was placed in a 100 mL eggplant bottle in turn.The temperature was raised to 80 C for 2 hours. After the reaction was completed, the solvent was evaporated, and the residue was dissolved in dichloromethane (100 mL).Wash the organic layer with 2N hydrochloric acid (100 mL), and wash several layers with saturated aqueous sodium carbonate (100 mL).The organic layer was washed with distilled water, dried over anhydrous sodium sulfate, evaporated and evaporated5.01 g of a yellow solid was obtained in a yield of 90.2%.
With 8-methylquinoline 1-oxide; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); at 20℃; for 8h;
General procedure: A mixture of 8-methylquinoline 1-oxide (62.0 mg, 0.39 mmol), MsOH (32.4 mg, 0.33 mmol), and Ph3PAuNTf2 (11.4 mg, 0.015mmol) was added to a soln of the appropriate alkyne 1 (0.30 mmol) in AcOH (5 mL), and the mixture was stirred at r.t. until the reaction was complete (TLC). The mixture was then concentrated and the residue was purified by chromatography (silica gel, hexanes-EtOAc).
In dichloromethane; water; at 50℃;Green chemistry;
General procedure: A 10-mL round flask was charged with PhI(OAc)2 (0.24mmol, 77.3 mg) and enamides 1 (0.2 mmol, 1.0 equiv.) inCH2Cl2/H2O (2.0 mL, v/v=1:1). The flask was heated to50 C under vigorous stirring. Upon completion (detectedby thin layer chromatography (TLC)) of the reaction, thereaction mixture was cooled down to room temperature. Itwas quenched with H2O (5 mL) and extracted with EtOAc(2×10 mL). The combined organic layers were dried over anhydrousNa2SO4 and then evaporated in vacuo. The residuewas purified by column chromatography on silica gel withhexane/ethyl acetate (v/v=6:1) as the eluent to afford thecorresponding product 2.
With boron trifluoride diethyl etherate; In 5,5-dimethyl-1,3-cyclohexadiene; for 30h;Reflux;
2-(4-Bromophenyl)-2-oxoethyl acetate (12.38 g, 45.7 mmol, 1 equiv), xylene(120 mL), acetamide (13.50 g, 229 mmol, 5 equiv), boron trifluoride etherate (2.285 mL) were sequentially added to 250 mL of eggplantIn a row bottle, the temperature was raised to reflux reaction, and the reaction was carried out for 30 hours. After the reaction is completed, xylene is distilled off, and the residue is dissolved in dichloromethane, and steamed.The dichloromethane layer was washed with distilled water, dried over anhydrous sodium sulfate and evaporated.Flash column chromatography gave 3.06 g of a yellow solid.The yield was 26.6%.
In acetonitrile; at 100℃; for 0.666667h;Sealed tube; Microwave irradiation;
General procedure: A mixture offormamidinium acetate (2c, 54 mg, 0.52 mmol), K2CO3 anhydrous (141 mg, 1.02 mmol),and the appropriate substrate 1a-d (1.00 mmol) in acetonitrile anhydrous (1.0 mL) wassubjected to microwave irradiation at 120 C (150 W, monitored by an IR temperaturesensor) and maintained at this temperature for 40 min in a sealed tube containing a Tefloncoatedmagnetic stirring bar. The reaction treatment and purification of the products werecarried out in the same way as in the previous reaction. The first fraction eluted by flashchromatography contained N-aroylmethylimidazoles 3i-l (major product, 68-72%), whilethe second fraction contained compounds 4i-j (minor product, 17-22%). Aroylmethylacetates 5a-d were obtained when this reaction was carried out at 100 C under similarconditions; however, the residue obtained was purified by flash chromatography (eluent:CH2Cl2) to afford the pure products 5a-d in high yields (82-87%).