Entry | p-TsCl (mol%) | Solvent | Temperature (°C) | Time (min) | Yield (%) a |
---|---|---|---|---|---|
1 | 0 | - | 110 | 120 | No reaction |
2 | 10 | - | 90 | 25 | 82 |
3 | 10 | - | 110 | 15 | 87 |
4 | 5 | - | 90 | 35 | 80 |
5 | 5 | - | 110 | 15 | 86 |
6 | 5 | - | Rt | 240 | Trace |
7 | 3 | - | 110 | 75 | 28 |
8 | 10 | CH2Cl2 | Rt | 1,050 | 19 |
9 | 5 | CH2Cl2 | Rt | 1,050 | Trace |
10 | 10 | THF | Rt | 600 | Trace |
11 | 10 | CH3CN | Rt | 720 | 17 |
12 | 10 | CH2Cl2 | Reflux | 300 | 36 |
13 | 50 | - | 110 | 5 | 43 (tosylate: 47) |
14 | 100 | - | 110 | 5 | 7 (tosylate: 91) |