Table 1.
Entry |
Initiator |
mol % |
Time |
Yield [%][a] |
---|---|---|---|---|
1 |
tBuOLi |
10 |
1 h |
91 |
2 |
Me3SiOLi |
10 |
1 h |
>95 |
3 |
Me3SiONa |
10 |
<5 min |
98 (70)[b] |
4 |
Me3SiOK |
10 |
<5 min |
90 |
5 |
Me3SiONa |
5 |
<5 min |
>95 |
6 |
Me3SiONa |
1 |
20 h |
6 |
7 |
Me3SiOK |
1 |
20 h |
58 |
8 |
CsF |
10 |
20 h |
60 |
9 |
TMAF |
10 |
20 h |
trace |
[a] Determined by calibrated GLC analysis with tetracosane as an internal standard. [b] Yield of isolated product on a 0.40 mmol scale after flash chromatography on silica gel in parentheses. TMAF=tetramethylammonium fluoride.