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Reaction id: 0601011005_06, verified by Personal Chemistry ©
Methyl 2-Acetami...
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5f
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Hydroquinone
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DMF
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6f
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Yield: 48% Time: 3600s Temperature: 200 °C
Chemicals
| Name |
MW [g/mol] |
Density [g/ml] |
Amount [mmol] |
Mass/Volume |
| 35356-70-8 |
143.142 |
1.000 |
2.249 |
321.976 µl |
| Substrate 1 |
222.287 |
1.000 |
0.450 |
100.000 mg |
| Hydroquinone |
110.112 |
1.000 |
0.045 |
4.954 mg |
| DMF |
73.095 |
0.940 |
12.860 |
1000.000 µl |
| Product 1 |
365.429 |
1.000 |
0.000 |
0.000 µl |
Keywords
2+4 Cycloaddition, Cycloaddition, Diels-Alder Reaction, Regioselective
Comments
Synthesis: This reaction was also carried out using conventional heating, and then required 135-165°C for 2 to 3 days. Even then, it didn't give very high yields, and more of the regioisomer where the bridge substituent is ortho to the anthracene substituent. In this case, the ratio between these was >99:1. Independent of heating method, higher temperatures were found to suppress formation of the ortho product, probably due to the higher thermodynamic stability of the meta compound.
Analysis: HPLC was used to determine the regioisomer ratio and the conversion of anthracene to product, in this case 50%.
Purification: The product was isolated by column chromatography.
Instrument Settings
Absorption level: Normal
Pre-stirring time: 0s
References
Yang, B. V.; Doweyko, L. M. Tet. Lett. 2005, 46, 2857-2860
Analysis
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