Uses
TRIMETHYLSILYLBENZENESULFONATE is used for the lithio anion reacts with carbonyl compounds to afford vinyl sulfones via a modified Peterson alkenation procedure; double alkylation, reduction, and sila-Pummerer rearrangement provides ketones.
Synthesis Reference(s)
1. Craig, D.; Ley, S. V.; Simpkins, N. S.; Whitham, G. H.; Prior, M. J. JCS(P1) 1985, 1949.
2. Cooper, G. D. JACS 1954, 76, 3713.
Synthesis
Trimethylsilylbenzenesulfonate can be readily synthesized via several routes,
1of which the most suitable for large-scale preparation involves the reaction of sodium thiophenolate with (Chloromethyl)trimethylsilane, the sulfide obtained then being oxidized to the sulfone with buffered Peracetic Acid.
2
Purification Methods
Fractionate it at high vacuum and recrystallise it from pentane at -80o. If too impure (cf IR), dissolve it in CH2Cl2 (ca 800mL for 100g), wash this with 2M aqueous NaOH (2 x 200mL), brine, dry, evaporate and distil it. [Craig et al. J Chem Soc, Perkin Trans 1 1949 1985, IR and NMR: Cooper J Am Chem Soc 76 3713 1954.]
