Table 2.
entry | alcohol | product | yield (%)b | d.r.c |
---|---|---|---|---|
1d | Me2CHCH2OH | 97 | 10:1 | |
2d | Me(CH2)5OH | 86 | 7:1 | |
3d | TMS(CH2)3OH | 88 | 5:1 | |
4 | CH2=CH(CH2)4OH | 63 | 5:1 | |
5 | PhCH2OH | 90 | 1.2:1 | |
6 | 4-ClPhCH2OH | 82 | 1:1 | |
7 | 4-MeOPhCH2OH | 85 | 1:1 | |
8 | PhCH(OH)Me | 67 | 2.5:1 | |
9 | cyclohexanon | 68 | n.a. |
Alcohol (1.5 equiv), EtMgBr (2.0 equiv), 0 °C → rt; then 1 (1.0 equiv).
Isolated yield.
Determined by 1H NMR spectroscopy; the major isomer is shown.
Reaction solvent: 2:1 THF/CH2Cl2.