Table 2.
Entry | Condition | Yield (%) a | |
---|---|---|---|
19 | 20 | ||
1 | H2, Pd/C (3 mol %), MeOH, rt | 65 | - |
2 | TMSI b, CH2Cl2, rt | - | 60 |
3 | HBr (47%), 50 °C | - | 60 |
4 | TiCl4 (1 eq), CH2Cl2, 0 °C | NR c | |
5 | Li, naphthalene, THF, −25 °C | NR |
a Isolated yield; b trimethylsilyl iodide; c no reaction.