Table 1. Synthesis of propargyl ethers and esters (8 → 7).
| Compound | Base | X | Solvent | t, h | T, °C | Yield, % |
|---|---|---|---|---|---|---|
| 7a | K2CO3 | Br | Me2CO | 25.5 | 56 → r.t. | 95 |
| 7b | K2CO3 | Br | Me2CO | 17.5 | r.t. | 94 |
| 7c | K2CO3 | OMs | DMF | 24 | 80 | 33 |
| 7d | K2CO3 | Br | DMF | 24 | 60 | 24 |
| 7e | K2CO3 | Br | DMSO | 24 | 65 | 43 |
| 7fa | NaOH | Br | DMF | 20 | r.t | 14 |
| 7g | NaH | Br | DMF | 17.5 | 0 → 40 | 57 |
| 7h | NaOH | Br | DMF : Hex = 4 : 3 | 12 | r.t | 57 |
| 7i | NaOH | Br | DMF : Hex = 1 : 1 | 24 | r.t | 23 |
KI (0.1 eq.) was added.