Table 1: Effect of the ratio of α-olefin to SMB on isolated yield.
|
Entrya
|
α-olefin
|
α-olefin: SMB mole ratiob
|
Yield (%)
|
| 1 |
C26-28
|
1:3 |
40 |
| 2 |
C18
|
1:3 |
43 |
| 3 |
C26-28
|
1:2 |
45 |
| 4 |
C26-28
|
2:1 |
46 |
| 5 |
C18
|
1:2 |
47 |
| 6 |
C26-28
|
3:1 |
48 |
| 7 |
C18
|
2:1 |
52 |
| 8 |
C18
|
3:1 |
57 |
| 9 |
C18
|
1:1 |
70 |
| 10 |
C26-28
|
1:1 |
71 |
aAll compounds have been characterized by GC and 1H NMR. bAll reactions carried out under N2 using THF. Cannula additions were carried out dropwise over the course of 45-60 minutes. Following the cannula transfer, the reaction mixture was heated to 160 °C for 5 hours.