Optimizing of the reaction conditions for the synthesis of 2ha.
| |||||
|---|---|---|---|---|---|
| Entry | Solvent | Temperature (°C) | Catalyst loading (mg) | Time (min) | Yieldb (%) |
| 1 | — | 90 | 10 | 10 | 92 |
| 2 | — | 80 | 15 | 10 | 90 |
| 3c | — | 70 | 10 | 10 | 91 |
| 4 | 70 | 5 | 30 | 80 | |
| 5 | — | 70 | — | 10 | Trace |
| 6 | — | 70 | 7 | 10 | 82 |
| 7 | — | 70 | 20 | 10 | 92 |
| 8 | — | 70 | — | 120 | 60 |
| 9 | — | 60 | 10 | 30 | 70 |
| 10 | — | 50 | 10 | 100 | 20 |
| 11 | H2O | Reflux | 10 | 60 | — |
| 12 | EtOH | Reflux | 10 | 60 | 45 |
| 13 | n-Hexane | Reflux | 10 | 60 | — |
| 14 | EtOAc | Reflux | 10 | 60 | 50 |
| 15 | CH2Cl2 | Reflux | 10 | 60 | — |
Reaction conditions: 4-cholorobenzaldehyde (1 mmol, 0.140 g), 5,5-dimethylcyclohexane-1,3-dione (1 mmol, 0.140), ethyl acetoacetate (1 mmol, 0.130 g), ammonium acetate (1 mmol, 0.078 g).
Related to isolated yields.
Optimal data.