Table 1. Optimization of reaction conditionsa.
| |||||
|---|---|---|---|---|---|
| S. no. | Base | Solvent | Temp./time | Yield (3a) | Yield (3a′) |
| 1 | K2CO3 | 1,4-Dioxane | 60 °C, 6 h | 20% | — |
| 2 | K2CO3 | THF | 60 °C, 6 h | 40% | — |
| 3 | Cs2CO3 | 1,4-Dioxane | 60 °C, 6 h | 24% | — |
| 4 | Cs2CO3 | THF | 60 °C, 6 h | 50% | — |
| 5 | Cs2CO3 | THF–H2O (5 : 2) | 60 °C, 6 h | 60% | — |
| 6 | Na2HPO4 | THF | 60 °C, 6 h | 82% | — |
| 7 | Na2HPO4 | THF–H2O (5 : 2) | 60 °C, 6 h | 91% | 1% |
| 8 | Na2HPO4 | THF–H2O (4 : 3) | 60 °C, 6 h | 80% | 2% |
| 9 | Na2HPO4 | THF–H2O (3 : 4) | 60 °C, 6 h | 75% | Trace |
| 10 | TEA | THF | 60 °C, 6 h | Trace | Trace |
Reaction conditions: 1a (0.0187 mmol), 2 (0.0187 mmol), Na2HPO4 (0.02 mmol), 6 h, and temperature 60 °C in sealed tube.