Sodium Azide → 2-(Azidomethyl)oxane
Reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1>CS(C)=O>[N:1]([CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1)=[N+:2]=[N-:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A mixture of sodium azide (65 g, 1 mol), dimethylsulfoxide (800 ml), and 2-(bromomethyl)-tetrahydro-2H-pyran (89.5 g, 0.5 mol) is stirred at 50° C. for 12 hours. The reaction mixture is allowed cool to room temperature and then slowly poured into ice water. The reaction is extracted with ether (3×400 ml). The combined organic extracts are washed with water (500 ml) and then brine (500 ml), and dried over sodium sulfate. Removal of the volatiles in vacuo affords the pure title compound (62 g, 88%) as a colorless oil.
Workup
- temperatureThe reaction mixture is allowed cool to room temperature
- extractionThe reaction is extracted with ether (3×400 ml)
- washThe combined organic extracts are washed with water (500 ml)
- dry with materialbrine (500 ml), and dried over sodium sulfate
- customRemoval of the volatiles in vacuo
Sources & evidence
- ORD record
- ord-4c7a62e8340f4301bddbbd88a45b9e32
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06642390B2
Reaction notes
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