tert-Butyldimethylsilyl chloride → (2-Azidoethoxy)(tert-butyl)dimethylsilane

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Reaction Steps

Scheme 1 shows the general method of synthesis. 2-Azidoethanol, (1), is treated with tert-butylchlorodimethylsilane to produce 1-azido-2-(tert-butyldimethylsiloxy)ethane (2). This is then treated with methyllithium (or other organometallic) to produce the corresponding 3-alkylated triazene (3). This compound is then acylated (4) either by treatment with an isocyanate or by treatment with KH in presence of a phase transfer catalyst to form an anion followed by reaction with an acyl halide, acid anhydride or similar acylating agents. The hydroxy group is then deprotected by treatment with tetra-n-butylammonium fluoride to produce the 2-hydroxyethyl triazene (5), and the chloride is then produced by reaction with Ph3P/CCl4 (6).

Provenance & Evidence