Table 1. Screenings of the Acid Loadingsa.
entry | loading (mol %) | conv. (%)b | entry | loading (mol %) | conv. (%)b |
---|---|---|---|---|---|
1 | 0.005 | 68 | 14 | 30 | 91 |
2 | 0.01 | 76 | 15 | 60 | 89 |
3 | 0.03 | 91 | 16 | 100 | 84 |
4 | 0.05 | 93 | 17 | 120 | 78 |
5 | 0.10 | 95 | 18 | 300 | 59 |
6 | 0.20 | 94 | 19 | 600 | 6 |
7 | 0.25 | 94 | 20c | 0.10 | 93 |
8 | 0.30 | 95 | 21d | 0.10 | 93 |
9 | 0.5 | 92 | 22e | 0.10 | 96 |
10 | 1.0 | 92 | 23f | 0.10 | 93 |
11 | 3.0 | 92 | 24g | 0.10 | 91 |
12 | 6.0 | 92 | 25h | 0.10 | 92 |
13 | 12 | 91 | 26i | 0.10 | 91 |
Unless otherwise specified, a mixture of aldehydes 1 (2 mmol) and hydrochloric acid in methanol was stirred at an ambient temperature for 20 min.
Determined by gas chromatography (GC) analyses of the crude reaction mixture.
At 50 °C for 3 min.
At 30 °C for 10 min.
At 0 °C for 2 h.
At −20 °C for 2 h.
At −60 °C for 24 h.
8 mol/L HCl was used.
4 mol/L HCl was used.