| Identification | Back Directory | [Name]
t-Butyl α-Lithiobis(trimethylsilyl)acetate | [CAS]
62803-13-8 | [Synonyms]
t-Butyl a-Lithiobis(trimethylsilyl)acetate
Lithium enolate of t-butyl-bistrimethylsilylacetate
Acetic acid, bis(trimethylsilyl)-, 1,1-dimethylethyl ester, ion(1-), lithium | [Molecular Formula]
C12H27LiO2Si2 | [MDL Number]
MFCD16876451 | [MOL File]
62803-13-8.mol | [Molecular Weight]
266.46 |
| Hazard Information | Back Directory | [Synthesis]
Synthesis method of t-Butyl α-Lithiobis(trimethylsilyl)acetate: An approximately 1 M solution in THF is prepared by addition of t-butyl bis(trimethylsilyl)acetate to a 1.0 M solution of Lithium Diisopropylamide maintained at -78 °C. The solution is stirred for 1 h at -78 °C following complete addition.1 A simplified procedure utilizes n-Butyllithium in place of LDA and produces the amine-free reagent in THF/hexane.2
| [Uses]
T-Butyl a-Lithiobis(trimethylsilyl)acetate reacts with aldehydes to form α-silylated vinyl esters.
| [Synthesis Reference(s)]
1. Hartzell, S. L.; Rathke, M. W. TL 1976, 2737.
2. Sato, Y.; Takeuchi, S. S 1983, 734.
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