Table 2. Rearrangement of 8a to 6a: selected optimization.
| |||
| Entry | Conditions a | Conversion b | Yield c |
| 1 | 5 equiv. 16, MeOH, 170 °C, 8 h d | 46% | 13% |
| 2 | 5 equiv. 16, MeOH, 120 °C (mW), 12 h | N.D. | 21% |
| 3 | 0.4 equiv. 16, MeOH, 120 °C (mW), 8 h | N.D. | 32% e |
| 4 | 0.4 equiv. 16, HFIP, 150 °C (mW), 3 h | 45% | 47% e , f |
| 5 | 0.4 equiv. 16, HFIP, 150 °C (mW), 3 h | 58% | 56% e , f , g |
a[8a] = 0.1 M (0.075 mmol).
bConversion was calculated based on the recovery of 8a.
cIsolated yield after column chromatography.
dThe reaction was carried out in a sealed tube.
eThe reaction vial was pretreated by N,O-bis(trimethylsilyl)acetamide.
f[8a] = 0.5 M (1 mmol).
gThe heating sequence was composed of 12 cycles with each cycle including irradiation at 150 °C for 15 min and at 50 °C for 15 min.