Water → Ethyl 4-azidobutanoate

HRID 964290Notes

Reaction equation

HRID 964290 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[N-:10]=[N+:11]=[N-:12].[Na+].O>CO>[N:10]([CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:11]=[N-:12]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 12382175Ethyl 4-azidobutanoateYield 98.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 4-bromobutyrate (10.0 g, 51.3 mmol), NaN3 (6.66 g, 102 mmol) and 25 ml of water in 75 ml of MeOH was refluxed for 3.5 hrs. The MeOH was removed in vacuo and residue was partitioned between CHCl3 (200 ml) and water (50 ml). The organic layer was separated and washed with water. After drying and evaporation of solvent, ethyl 4-azidobutyrate (7.94 g, 98.6%) was obtained as a colorless oil.

Workup

  1. customThe MeOH was removed in vacuo and residue
  2. customwas partitioned between CHCl3 (200 ml) and water (50 ml)
  3. customThe organic layer was separated
  4. washwashed with water
  5. customAfter drying
  6. customevaporation of solvent

Sources & evidence

ORD record
ord-4216cb94fc8f47f48f362fac784c7a19
Source dataset
uspto-grants-1998_06
Patent number
US05767131

Reaction notes

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