Table 1.
Optimization of the reaction conditions a.
| Entry | Base | Temp. (°C) | Solvent | Time (min) | Yield (%) b |
|---|---|---|---|---|---|
| 1 | K2CO3 | MW 80 | DCE | 10 | 27 c |
| 2 | Na2CO3 | MW 80 | DCE | 10 | 21 |
| 3 | NaOH | MW 80 | DCE | 10 | 12 |
| 4 | NaHCO3 | MW 80 | DCE | 10 | 17 |
| 5 | tBuOLi | MW 80 | DCE | 10 | complex |
| 6 | DABCO | MW 80 | DCE | 10 | 19 |
| 7 | DBU | MW 80 | DCE | 10 | 45 |
| 8 | TEA | MW 80 | DCE | 10 | 23 |
| 9 | DBU | MW 80 | DMSO | 10 | 29 |
| 10 | DBU | MW 80 | DMF | 10 | 31 |
| 11 | DBU | MW 80 | Toluene | 10 | 13 |
| 12 | DBU | MW 80 | THF | 10 | <10 |
| 13 | DBU | MW 80 | MeCN | 10 | 57 |
| 14 | DBU | MW 80 | EtOH | 10 | trace |
| 15 | DBU | MW 80 | Dioxane | 10 | 43 |
| 16 | DBU | MW 80 | 1-hexanol | 10 | 32 |
| 17 | DBU | MW 80 | N-ethylpyrrolidone | 10 | 40 |
| 18 c | DBU | MW 80 | MeCN | 10 | 61 |
| 19 c | DBU | MW 100 | MeCN | 10 | 72 |
| 20 c | DBU | MW 120 | MeCN | 10 | 72 |
| 21 | DBU | MW 100 | MeCN | 5 | 58 |
| 22 | DBU | MW 100 | MeCN | 15 | 71 |
| 23 | DBU | 100 | MeCN | 1 h | 51 |
a Reaction conditions: 1a (0.3 mmol), 2a (0.3 mmol), Base (1.0 equiv.), solvent (3.0 mL). b Isolated yield. c 30 mol% DBU. Most of the starting materials were left.