Table 1.
Optimization of reaction conditionsa.
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entry | modified reaction conditions | yields of 2 (%)b |
1 | none | 67 (58) |
2 | with 1 M (0.5 mL, 0.5 mmol) HCI | 0 |
3 | with 3 M (0.5 mL, 1.5 mmol) HCI | 20 |
4 | 3 h instead of 6 h | 48 |
5 | with 3 mmol p-TsOH | 55 |
6 | with 3 mmol TfOH | 62 |
7 | with 3 mmol AcOH | 63 |
0.1 mmol scale reactions in 0.5 mL solvent.
1H NMR yields using pyrene as an internal standard. Value in parenthesis is the isolated yield from 0.5 mmol.