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Reaction id: 0801011008_12, verified by Personal Chemistry ©
2a
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1j
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(Ph3P)4Pd
Cs2CO3
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EtOH
Toluene
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4l
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Yield: 90% Time: 600s Temperature: 150 °C
Chemicals
| Name |
MW [g/mol] |
Density [g/ml] |
Amount [mmol] |
Mass/Volume |
| 40138-16-7 |
149.941 |
1.000 |
0.600 |
89.965 mg |
| Substrate 1 |
264.049 |
1.000 |
0.500 |
132.025 mg |
| (Ph3P)4Pd |
1155.570 |
1.000 |
0.020 |
23.111 mg |
| Cs2CO3 |
325.818 |
1.000 |
1.500 |
488.727 mg |
| Toluene |
92.141 |
0.870 |
18.884 |
2000.000 µl |
| EtOH |
46.069 |
0.810 |
17.582 |
1000.000 µl |
| Product 1 |
271.241 |
1.000 |
0.000 |
0.000 mg |
Keywords
Aldol condensation, Cascade reaction, Condensation, Cyclisation, Ring closure, Ring formation, Suzuki Coupling
Comments
Synthesis: This phenanthrene synthesis was first carried out in two steps, but they were possible to combine using the conditions described here. Many bases and solvent systems were tested, and it was found that the ones presented here gave the best results. The ratio between toluene and ethanol was found to be very important. For some less reactive substrates, SPhos or DavePhos was used as additives (see 0801011008_07, _13-_14 and _19-_22). When one of the reactions was carried out with conventional heating, it gave a similar yield (81% compared to 87% with microwaves), but required 2 hours to reach completion.
The reaction was carried out under dry nitrogen.
Work-up and purification: After the reaction, the mixture was diluted with ethyl acetate and filtered through a celite pad. The solvents were then removed and the product purified by silica column chromatography.
Characterisation: By mp, 1H NMR, 13C NMR, IR and HRMS.
Instrument Settings
Absorption level: Normal
Pre-stirring time: 0s
References
Kim, Y. H.; Lee, H.; Kim, Y. J.; Kim, B. T.; Heo, J.-N. J. Org. Chem. 2008, 73, 495-501
Analysis
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