Table 1.
| |||||
---|---|---|---|---|---|
entry | nucleophile | reaction time (h) | product | isolated yield (%) | |
1 | 3 | 2a | 98 | ||
2 | 5 | 2b | 97 | ||
3 | 11 | 2c | 91b | ||
4 | 7 | 2d | 99 | ||
5 | 5 | 2e | 75 | ||
6 | 24 | 2f | 95 | ||
7 | 6 | 2g | 86 | ||
8 | MeONa | 14 | 2h | 91b | |
9 | 3 | 2i | 84 | ||
10 | 5 | 2j | 98 | ||
11 | 5 | 2k | 92 |
Conditions: ROH (3 equiv), NaH (3 equiv), THF (0.2 M), 0 °C–rt.
Commercially available alkoxide was used.