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Reaction id: 0801011009_01, verified by Personal Chemistry ©
7a
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6
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Acetic acid
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5a
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Yield: 83% Time: 300s Temperature: 230 °C
Chemicals
| Name |
MW [g/mol] |
Density [g/ml] |
Amount [mmol] |
Mass/Volume |
| 59-88-1 |
144.605 |
1.000 |
1.500 |
216.908 mg |
| Substrate 1 |
300.988 |
1.000 |
1.000 |
300.988 mg |
| Acetic acid |
60.052 |
1.050 |
87.424 |
5000.000 µl |
| Product 1 |
168.199 |
1.000 |
0.000 |
0.000 mg |
Keywords
Condensation, Cyclisation, Fischer Indole Synthesis, Heterocyclic, Heterocyclisation, Ring closure, Ring formation
Comments
Synthesis: When attempted using conventional heating at reflux temperature, the reaction required 12 h to reach completion. This method also gave lower yields (on average 10% lower isolated yield than with microwave heating).
Work-up and purification: After the reaction, the mixture was neutralised by adding Na2CO3 in water and then extracted with 3x20 ml ethyl acetate. The organic phase was dried over Na2SO4, concentrated and the product purified by column chromatography on silica eluted with petroleum ether/ethyl acetate/ethanol.
Characterisation: By mp, 1H NMR, 13C NMR, MS and elemental analysis.
Instrument Settings
Absorption level: Normal
Pre-stirring time: 0s
References
Chen, J.; Chen, W.; Hu, Y. Synlett 2008, 77-82
Analysis
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