Chemical Properties
CLEAR COLOURLESS LIQUID
Physical properties
bp 50–52 °C/10 mmHg, 71–73 °C/35 mmHg;
d 0.825 g cm?3.
Uses
2-(Trimethylsilyl)ethanol is a protecting reagent for carboxyl, phosphoryl, hydroxyl, and amino
groups. It participates in the reactions of Phenol and Acid Protection, Alcohol Protection, Hemiacetal Protection, Amine Protection, Enol Ether Synthesis, Carbohydrate Chemistry etc.
Uses
Used to synthesize Teoc-protected amines via alcoholysis of the corresponding isocyanates.
Uses
2-(Trimethylsilyl)ethanol is used as a protecting reagent for carboxyl, phosphoryl, hydroxyl and amino group in organic synthesis. It is used as a precursor to prepare trimethyl(2-phenoxyethyl)silanes by reacting with aromatic fluoride. It is also used in the synthesis of teoc-protected amines by using the corresponding isocyanates.
Preparation
Three methods of preparation have been
reported: (a) from the treatment of ethyl bromoacetate with
zinc followed by the reaction with chlorotrimethylsilane1 and
subsequent reduction of the resultant ethyl trimethylsilylacetate
with lithium aluminum hydride2,3 or borane¨Ctetrahydrofuran(eq 1); (b) from the hydroboration/oxidation or oxymercuration/demercuration of vinyltrimethylsilane (eq 2); and (c)most conveniently, by the reaction of the Grignard reagent
formed from (chloromethyl)trimethylsilane with paraformaldehyde
(eq 3).
Purification Methods
If the NMR spectrum is not clean, then dissolve the alcohol in Et2O, wash it with aqueous NH4Cl solution, dry (Na2SO4), evaporate and distil it. The 3,4-dinitrobenzoyl derivative has m 66o (from EtOH). [NMR: Speier et al. J Am Chem Soc 79 974 1957, Z Naturforsch 14b 137 1959, Beilstein 4 IV 3951.]
