Sodium Azide → Azidomethyl 2,2-dimethylpropanoate
Reaction equation
[C:1]([O:7][CH2:8]Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[N-:10]=[N+:11]=[N-:12].[Na+]>O>[C:1]([O:7][CH2:8][N:10]=[N+:11]=[N-:12])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
Chloromethyl pivalate (1.93 ml, 12.9 mmol) and sodium azide (1.27 g, 19.3 mmol) were taken up in water (52 ml). The reaction mixture was heated to 90° C. for 22 hours. The reaction mixture was cooled to ambient temperature, and extracted with ethyl acetate three times. The organic layers were combined, washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford the title compound.
Workup
- temperatureThe reaction mixture was cooled to ambient temperature
- extractionextracted with ethyl acetate three times
- washwashed with brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-15529bdcea904d63961c709190d9b360
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367706B2
Reaction notes
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