The study results on the effect of various solvents on the A3-coupling preparation of propargylaminea.
Entry | Solvent | Base | Temp. (°C) | Cat. (mol%) | Time (h) | Yieldb (%) |
---|---|---|---|---|---|---|
1 | CH3CN | KOH | 60 | 0.05 | 10 | 75 |
2 | CH3CN | KOH | 60 | 0.1 | 10 | 75 |
3 | EtOH | KOH | 80 | 0.05 | 10 | 45 |
4 | EG | KOH | 100 | 0.05 | 10 | 61 |
5 | CHCl3 | K2CO3 | 60 | 0.1 | 10 | 92 |
6 | CHCl3 | Cs2CO3 | 60 | 0.1 | 10 | 96 |
7 | CHCl3 | KOH | 60 | 0.1 | 10 | 87 |
9 | CHCl3 | NaOH | 60 | 0.1 | 10 | 84 |
10 | CHCl3 | Et3N | 60 | 0.1 | 10 | 76 |
Reaction conditions: 1.2 mmol of morpholine, 1 mmol of benzaldehyde, and 1.3 mmol of phenylacetylene.
Isolated yields.