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Reaction id: 0601011048_21, verified by Personal Chemistry ©
4-Methylphenylhy...
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14 (1)
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EtOH
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26
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Yield: 95% Time: 300s Temperature: 160 °C
Chemicals
| Name |
MW [g/mol] |
Density [g/ml] |
Amount [mmol] |
Mass/Volume |
| 539-44-6 |
122.171 |
1.000 |
0.300 |
36.651 µl |
| Substrate 1 |
230.185 |
1.000 |
0.450 |
103.583 µl |
| (0.8 mmol/g, silica) |
0.000 |
1.000 |
1.500 |
1875.000 mg |
| EtOH |
46.069 |
0.810 |
87.912 |
5000.000 µl |
| Product 1 |
316.326 |
1.000 |
0.000 |
0.000 µl |
Keywords
Cyclisation, Heterocyclisation, Ring formation, Solid phase reagent
Comments
Synthesis: This reaction type was also carried out at room temperature, and gave the same high yield in 7 h with both silica-supported and free TsOH. With microwave heating, the yield dropped for free TsOH, but using the silica-supported reagent, the reaction was quick and clean. The enol ketone starting material was synthesised from substituted acetophenone and ethyl 2,2,2-trifluoroacetate (see 0601011048_09).
Work-up and purification: After the reaction, the solvent was removed under reduced pressure and the product purified by column chromatography on a Biotage SP4 system.
Characterisation: Full spectroscopic data was obtained.
Instrument Settings
Absorption level: Normal
Pre-stirring time: 0s
References
Humphries, P. S.; Finefield, J. M. Tet. Lett. 2006, 47, 2443-2446
Analysis
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