Table 1. Reaction optimization.a.
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.