Table 2.
Effect of the Number of Equivalents of MeOH and n-BuLia
 | |||||
|---|---|---|---|---|---|
| entry | solvent | MeOH (eq) | n-BuLi (eq) | yield (%)b | |
| 5a | 6ac | ||||
| 1 | CHCl3 | 2.0 | 1.0 | 37 | - |
| 2 | CH2Cl2 | 2.0 | 0.0 | 51 | 18 |
| 3 | CH2Cl2 | 2.0 | 1.0 | 71 | - |
| 4 | CH2Cl2 | 1.5 | 1.0 | 61 | - |
| 5 | CH2Cl2 | 1.0 | 1.0 | 49 | - |
| 6 | CH2Cl2 | 3.0 | 1.0 | 62 | 11 |
| 7 | CH2Cl2 | 1.25 | 0.25 | 58 | 4 |
| 8 | CH2Cl2 | 3.0 | 2.0 | 64 | - |
| 9 | CH2Cl2 | 4.0 | 3.0 | 52 | |
| 10 | CH2Cl2 | 4.0 | 2.0 | 66 | - |
| 11 | CH2Cl2 | 6.0 | 3.0 | 59 | |
a
See the Supporting Information for a detailed experimental procedure.
b
Isolated yields.
c
Stereochemistry of the alkene was exclusively E (NOESY NMR spectroscopy).