Table 1. Reaction optimization.a.
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|---|---|---|---|---|
| Entry | Solvent | HCl source | Conc. | Conv./%a |
| 1 | DCE | HCl•DMPU | 1.0 | 64 |
| 2 | CH3CN | HCl•DMPU | 1.0 | 22 |
| 3 | CH3NO3 | HCl•DMPU | 1.0 | 30 |
| 4 | EtOAc | HCl•DMPU | 1.0 | 90 |
| 5 | DMSO | HCl•DMPU | 1.0 | 18 |
| 6 | EtOAc | HCl•DMPU | 0.5 | 89 |
| 7 | EtOAc | HCl•DMPU | 0.2 | 99 |
| 8 | EtOAc | HCl, Et2O | 0.2 | 32 (98)b |
| 9 | EtOAc | HCl, 2-propanol | 0.2 | 99c |
| 10 | EtOAc | HCl, dioxane | 0.2 | 65 (94)b |
| 11 | EtOAc | HCl, AcOH | 0.2 | 99c |
| 12 | EtOAc | HCl, H2O | 0.2 | 29 (65)b |
| 13 | EtOAc | CH3COCl/EtOH | 0.2 | 99 |
| 14 | EtOAc | TMSCl/MeOH | 0.2 | 95 |
Determined by GC-MS with dodecane as the internal standard.
24 h
combined with thiolated side product.
