Water → Methyl 4-azidobutanoate
Reaction equation
[CH3:1][O:2][C:3](=[O:8])[CH2:4][CH2:5][CH2:6]Br.[N-:9]=[N+:10]=[N-:11].[Na+].O>CS(C)=O>[N:9]([CH2:6][CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:8])=[N+:10]=[N-:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 47.5 °C
Procedure
To a solution of methyl-4-bromobutyrate in DMSO (0.6 M) was added with stirring NaN3 (1.5 eq). The suspension was heated (45-50° C., oil bath) with stirring for 5 h. After cooling, H2O was added and the mixture extracted with Et2O. The organic extracts were washed with brine and dried over Na2SO4. The solvent was removed in vacuo and the crude oil used without further purification (99%).
Workup
- temperatureAfter cooling
- extractionthe mixture extracted with Et2O
- washThe organic extracts were washed with brine
- dry with materialdried over Na2SO4
- customThe solvent was removed in vacuo
- customthe crude oil used without further purification (99%)
Sources & evidence
- ORD record
- ord-922c7435902b486d99f0d73efd64851c
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07989438B2
Reaction notes
Loading…