Table 1. Optimization of Conditions for the Chalcone Synthesis (1 mmol scale)a.
| Yield
(%)b |
||||
|---|---|---|---|---|
| Entry | Solvent/Surfactant | Base | 3a | 4a |
| 144 | EtOH | NaOH | 59 | 8 |
| 2 | H2O | NaOH | 70 | 0 |
| 3 | CTABc | NaOH | 56 | 11 |
| 4 | CTABd | NaOH | 65 | 9 |
| 5 | CTABe | NaOH | 61 | 8 |
| 6 | CTABd | KOH | 62 | 9 |
| 7 | CTABd | K2CO3 | 64 | 10 |
| 8 | CTABd | KOtBu | 64 | 9 |
| 9 | CTABd | DBUf | 34 | 15 |
| 10 | CTABd | DABCOg | 49 | 4 |
| 11 | CTABd | Piperidine | 44 | 3 |
| 12 | CTABd | TEAh | 57 | 5 |
| 13 | CTABd | C12H25(CH3)2N | - | - |
Reaction conditions: 5 mL vial, benzaldehyde (1 mmol), acetophenone (1 mmol), base (1 mmol); CTAB solution (1 mL), rt, 24 h.
The yields were estimated by 1H NMR with heptane as internal standard.
(at CMC; 0.9 mM, 0.033%).
(5 × CMC; 0.0045 M, 0.16%).
(61 × CMC; 54.9 mM, 2%).
1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU).
1,4-Diazabicyclo[2.2.2]octane (DABCO).
Triethylamine (TEA).