tert-Butyldimethylsilyl chloride → (2-Azidoethoxy)(tert-butyl)dimethylsilane
Reaction equation
[N:1]([CH2:4][CH2:5][OH:6])=[N+:2]=[N-:3].[C:7]([Si:11](Cl)([CH3:13])[CH3:12])([CH3:10])([CH3:9])[CH3:8]>>[N:1]([CH2:4][CH2:5][O:6][Si:11]([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:13])[CH3:12])=[N+:2]=[N-:3]Participants
3
Procedure
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).
Workup
- customthe general method of synthesis
Sources & evidence
- ORD record
- ord-4f897884f55a4c2cb175756a412108f3
- Source dataset
- uspto-grants-1990_05
- Patent number
- US04923970
Reaction notes
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