Water → Methyl 4-azidobutanoate

HRID 1669478Notes

Reaction equation

HRID 1669478 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

HCID 962WaterHCID 33557Sodium AzideHCID 107604Methyl 4-bromobutyrate

Product 1

HCID 13202491Methyl 4-azidobutanoate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

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

  1. temperatureAfter cooling
  2. extractionthe mixture extracted with Et2O
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo
  6. 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

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