Water → (5-Azido-3,3-dimethyl-pentyloxy)-tert-butyl-dimethyl-silane
Reaction equation
[C:1]([Si:5]([CH3:20])([CH3:19])[O:6][CH2:7][CH2:8][C:9]([CH3:18])([CH3:17])[CH2:10][CH2:11]OS(C)(=O)=O)([CH3:4])([CH3:3])[CH3:2].[N-:21]=[N+:22]=[N-:23].[Na+].O>CN(C)C=O>[N:21]([CH2:11][CH2:10][C:9]([CH3:18])([CH3:17])[CH2:8][CH2:7][O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:20])[CH3:19])=[N+:22]=[N-:23]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Step B To the solution of methanesulfonic acid 5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentyl ester (1.48 g, 4.96 mmol) in anhydrous dimethylformamide (10 mL) was added NaN3 (1.6 g, 25 mmol). The reaction mixture was heated at 60° C. for 18 h. The mixture was cooled, and water was added. The mixture was extracted with ethyl acetate twice. The combined organic layers were washed with saturated aqueous NaHCO3 solution, brine, dried over MgSO4 to give (5-azido-3,3-dimethyl-pentyloxy)-tert-butyl-dimethyl-silane as a yellow oil (0.8 g, 67%).
Workup
- temperatureThe mixture was cooled
- extractionThe mixture was extracted with ethyl acetate twice
- washThe combined organic layers were washed with saturated aqueous NaHCO3 solution, brine
- dry with materialdried over MgSO4
Sources & evidence
- ORD record
- ord-b1ea3d32424f42659c75e67141528033
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08354444B2
Reaction notes
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