Table 1.
Optimization of the reaction conditions [a].
Entry | Base | Solvent | T (°C) | Yield (%) [b] |
---|---|---|---|---|
1 | tBuOK | DMF [c] | 110 | 77 |
2 | tBuOK [d] | DMF [c] | 110 | 75 |
3 | tBuOK | DMF | 110 | 81 |
4 | tBuOK | DMF | 110 | 48 |
80 | ||||
5 | K2CO3 | DMF | 110 | 34 |
6 | K3PO4 | DMF | 110 | 55 |
7 | KOH | DMF | 110 | 27 |
8 | tBuOLi | DMF | 110 | 75 |
9 | NaOMe | DMF | 110 | 55 |
10 | tBuONa | DMF | 110 | 74 |
11 | tBuOK | DMF | 90 | 73 |
12 | tBuOK | DMF | 130 | 41 |
13 | tBuOK | DMAc | 110 | 54 |
14 | tBuOK | DMSO | 110 | 30 |
15 | tBuOK | Toluene | 110 | 9 |
16 | tBuOK | o-xylene | 110 | 12 |
17 | tBuOK | 1,4-dioxane | 110 | 15 |
[a] Reaction conditions: 1 (1 mmol), 2 (1.5 mmol), base (2.0 equiv.), solvent (1 mL), 110 °C, 16 h. [b] Isolated yields. [c] DMF (2 mL). [d] tBuOK (3 equiv.).