Table 1. Reaction Optimization Conditions.
entry | equiv 14 (x) | cosolvent, (vol) | time (h) | temp. (°C) | conversion (area %)a |
---|---|---|---|---|---|
1 | 1.2 | (0) | 2 | 100 | 63 |
2 | 1.2 | MeCN, (10) | 19 | 22 | 88 |
3 | 1.2 | MeCN, (10) | 3 | 40 | 90 |
4 | 1.2 | MeOH, (10) | 3 | 40 | 84 |
5 | 1.2 | DMSO, (10) | 3 | 40 | 87 |
6 | 1.2 | MeTHF, (10) | 3 | 40 | 79 |
7 | 1.2 | DCM, (10) | 3 | 40 | 77 |
8 | 1.2 | H2O, (10)b | 3 | 40 | 66 |
9 | 1.05 | MeCN, (5) | 3 | 35 | 90 |
9b | 28 | 35 | 89 | ||
10 | 1.05 | MeCN, (5) | 3 | 35 | 90 (80)c |
UPLC-UV percent area at 269 nm.
Total water was 20 vol.
Isolated yield.