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| reaction
monitoring by HPLC (% area) |
||||||
|---|---|---|---|---|---|---|
| entry | base (equiv) | solvents (M) | 1 | 3 | 4 | 5 |
| 1 | NaOAc (20) | MeOH (5) | 1–2 | 60–75 | 14–17 | 4–17 |
| 2 | NaOAc·3H2O (20) | MeOH (5) | 1–2 | 71–75 | 14–16 | 2–5 |
| NaHCO3 (0.5) | ||||||
| 3 | DIPEA (15) | MeOH (3) | 70 | ND | ND | ND |
| 4 | DABCO (15) | MeOH (3) | 87 | ND | ND | ND |
| 5 | DBU (10) | THF (10) | 72 | ND | ND | ND |
| 6 | K2CO3 (10) | THF (10) | 53 | ND | ND | ND |
| 7 | tBuOK (10) | THF (10) | 65 | 1.3 | ND | 4.1 |
| 8 | NaHCO3 (20) | MeOH (5) | 55 | 4 | ND | ND |
| 9 | K2CO3 (20) | MeOH (5) | 60 | ND | ND | ND |
ND = not detected.
