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Reaction id: 0401011010_10, verified by Personal Chemistry ©
s10
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NaOH
PPh3
Pd2(dba)3
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Water
DME
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p10
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Yield: 98% Time: 600s Temperature: 160 °C
Chemicals
| Name |
MW [g/mol] |
Density [g/ml] |
Amount [mmol] |
Mass/Volume |
| Substrate 1 (2.89M in DME) |
303.208 |
1.000 |
0.260 |
90.000 µl |
| PPh3 (0.2M in DME) |
262.292 |
1.000 |
0.011 |
53.000 µl |
| NaOH (2.08M in water) |
39.997 |
1.000 |
0.520 |
250.000 µl |
| Pd2(dba)3 (0.05M in DME) |
915.694 |
1.000 |
0.001 |
26.500 µl |
| DME |
90.122 |
0.867 |
0.765 |
79.500 µl |
| Water |
18.015 |
1.000 |
0.056 |
1.000 µl |
| Product 1 |
222.291 |
1.000 |
0.000 |
0.000 µl |
Keywords
Amination, Aromatic, Catalysis, Catalytic, Catalyzed, Cyclisation, Heterocyclisation, Metal, Ring closure, Ring formation, Substitution
Comments
Synthesis: The reaction was optimised with regards to catalyst, solvent system, ratios and concentrations of reactants and additives, time and temperature. The solvents (water and DME) were only added as parts of stock solutions. Here, they have been written out separately and 1 µl of each has been added to each protocol. This only to make them visible in the reaction scheme without getting warnings from the system.
Work-up: The reaction mixture was diluted with 15 ml ethyl acetate and washed with 10 ml brine, which was then extracted with 2*10 ml ethyl acetate. The combined organic fractions were dried over MgSO4 and filtered, and the solvent removed under reduced pressure.
Purification: The residue was dissolved in 5 ml dichloromethane and to this solution was added 250 mg washed Amberlyst 15 resin. The resulting mixture was stirred for 18 h, whereupon the resin was washed with 2*5 ml dichloromethane, 2*5 ml toluene and finally left to stand in 50% triethyl amine in dichloromethane for 1 h. After another washing, in 5 ml dichloromethane, the solutions were combined and the solvent removed to give the product.
Characterisation: The product was characterised by 1H NMR, 13C NMR, IR and HRMS.
Instrument Settings
Absorption level: Normal
Pre-stirring time: 0s
References
Brain, C. T.; Steer, J. T. J. Org. Chem. 2003, 68, 6814-6817
Analysis
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