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Reaction id: 0200001007_01, verified by Personal Chemistry ©
712
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862
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DCE
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0200001007_01
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Yield: 70% Time: 300s Temperature: 180 °C
Chemicals
| Name |
MW [g/mol] |
Density [g/ml] |
Amount [mmol] |
Mass/Volume |
| 15596073 |
302.313 |
1.000 |
0.375 |
113.367 mg |
| 6436904 |
193.246 |
1.031 |
0.250 |
46.859 µl |
| DCE |
98.960 |
1.250 |
31.578 |
2499.970 µl |
| Product 1 |
217.268 |
1.000 |
0.250 |
54.317 mg |
Keywords
Cascade reaction, Condensation, Heterocyclisation
Comments
Synthesis: Salts of amino acids must be deprotonated prior to the heating. This can be made either by adding triethylamine to the reaction mixture or by basic extraction to DCE. N,N-Dimethylformamide and toluene were also tried out as solvent, but in these solvents the reaction was much less successful. For less reactive carbonyls, such as ketones and sterically hindered esters, longer reaction times and/or higher temperatures were benificial.
Analysis: During the reaction triphenylphosphine oxide and diphenylmethylphosphine oxide are produced. If these by-products are neglected in the LCMS spectrum the purity is 76%.
Purification: The product was isolated by preparative RPLC. No further purification was done prior to the NMR experiment.
Characterisation: 1H NMR shifts (ppm): 1.36 (t, 3H, CH3), 3.72 (s, 2H, CH2), 3.98 (q, 2H, CH2, OEt), 4.57 (s, 2H, oxazolone), 5.06 (s, 1H, oxazolone), 7.24-7.37 (m, 5H, ArH).
Instrument Settings
Absorption level: Normal
Pre-stirring time: 0s
References
Schobert, R.; Löffler, J. Recent Res. Devel. in Org. & Bioorg. Chem. 1998, 2, 17-28
Analysis
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0200001007_01A.pdf