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Reaction id: 0601011033_03, verified by Personal Chemistry ©
4-Biphenylcarbox...
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Phenylacetic aci...
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PS-PPh3
CCl3CN
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MeCN
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3
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Yield: 94% Time: 1200s Temperature: 150 °C
Chemicals
| Name |
MW [g/mol] |
Density [g/ml] |
Amount [mmol] |
Mass/Volume |
| 92-92-2 |
198.221 |
1.000 |
0.100 |
19.822 mg |
| 937-39-3 |
150.181 |
1.000 |
0.110 |
16.520 mg |
| CCl3CN |
144.388 |
1.000 |
0.200 |
28.878 µl |
| PS-PPh3 (3.0 mmol/g, PS) |
261.284 |
1.000 |
0.300 |
100.000 mg |
| MeCN |
41.053 |
0.780 |
28.500 |
1500.000 µl |
| Product 1 |
312.372 |
1.000 |
0.000 |
0.000 µl |
Keywords
Condensation, Cyclisation, Heterocyclic, Heterocyclisation, Polymer Supported, Ring closure, Ring formation, Solid phase reagent
Comments
Synthesis: This method manages to combine the two steps normally needed for synthesis of 1,3,4-oxadiazoles, formation of a diacyl hydrazide and ring closure, without isolation of the intermediate. Using the conditions described here, the method is quite general and works well for a variety of aryl and alkyl acyl hydrazides and aryl and alkyl carboxylic acids.
Work-up and purification: After the reaction, the resin was filtered off and washed with acetonitrile. The product was isolated in a purity >98% by column chromatography.
Characterisation: By LCMS and 1H NMR.
Instrument Settings
Absorption level: Normal
Pre-stirring time: 0s
References
Wang, Y.; Sauer, D. R.; Djuric, S. W. Tet. Lett. 2006, 47, 105-108
Analysis
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