Sodium Azide → 8-Azido-1-octanol
Reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10].[N-:11]=[N+:12]=[N-:13].[Na+]>>[N:11]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10])=[N+:12]=[N-:13]Participants
3
Conditions
- Temperature
- 90 °C
Procedure
8-Bromo-octan-1-ol (2.61 g, 12.5 mmol) was dissolved in Dmf (30 mL) and sodium azide (0.89 g, 13.75 mmol) was added. The reaction was heated to 90° C. and stirred overnight. The solution was then cooled to room temperature and poured onto ice. The aqueous was extracted with DCM (3×200 mL) and the combined extracts were washed with brine (2×200 mL), then dried over MgSO4. The solution was filtered and the solvent was removed in vacuo to give a yellow oil, 1.99 g (93% yield);
Workup
- additionwas added
- temperatureThe solution was then cooled to room temperature
- additionpoured onto ice
- extractionThe aqueous was extracted with DCM (3×200 mL)
- washthe combined extracts were washed with brine (2×200 mL)
- dry with materialdried over MgSO4
- filtrationThe solution was filtered
- customthe solvent was removed in vacuo
- customto give a yellow oil, 1.99 g (93% yield)
Sources & evidence
- ORD record
- ord-fcc066106f89430980be7316c5a8396f
- Source dataset
- uspto-grants-1997_03
- Patent number
- US05610145
Reaction notes
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