Table 1. Reaction Developmenta.
entry | deviation from optimized conditions | time (h) | yield (%) |
---|---|---|---|
1 | noneb | 1 | 87 |
2 | no AcOH | 25 | complex |
3 | 20 mol % of AcOH in PhMe | 2 | complex |
4 | 20 mol % of BzOH in PhMe | 2 | complex |
5 | 5 equiv of AcOH in PhMe | 3 | 30 |
6 | 10 equiv of AcOH in PhMe | 3 | 38 |
7 | 20 equiv of AcOH in PhMe | 1.5 | 57 |
8 | PhMe/AcOH = 3:1c | 1.5 | 84 |
9 | PhMe/AcOH = 1:3d | 3.5 | 80 |
10 | AcOH as solvente | 3.5 | 73 |
11 | 0.2 M conc | 1 | 71 |
12 | 0.05 M conc | 1.5 | 87 |
Reactions were performed on a 0.2 mmol scale. All yields correspond to isolated yields.
Corresponds to 87.5 equiv of AcOH.
44 equiv of AcOH.
131 equiv of AcOH.
175 equiv of AcOH.