Water → Ethyl 4-azidobutanoate

HRID 322189Notes

Reaction equation

HRID 322189 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-e79a5d546683403ea96f5020e7fda7a8
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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