Water → HCID 12382177, compound

HRID 396688Notes

Reaction equation

HRID 396688 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[N-:12]=[N+:13]=[N-:14].[Na+].O>CO>[N:12]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N+:13]=[N-:14]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 117544Ethyl 6-bromohexanoate

Product 1

HCID 12382177HCID 12382177, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 6-bromohexanoate (10.0 g, 44.8 mmol), NaN3 (5.83 g, 89.6 mmol) and 25 ml of water in 75 ml of MeOH was refluxed for 3.5 hrs. The MeOH was removed in vacuo and the residue was partitioned between CHCl3 (200 ml) and water (50 ml). The organic layer was separated and washed with water. After drying (Na2SO4) and evaporation of solvent, ethyl 6-azidohexanoate (8.59 g, 100%) was obtained as a colorless oil.

Workup

  1. customThe MeOH was removed in vacuo
  2. customthe residue was partitioned between CHCl3 (200 ml) and water (50 ml)
  3. customThe organic layer was separated
  4. washwashed with water
  5. customAfter drying
  6. custom(Na2SO4) and evaporation of solvent

Sources & evidence

ORD record
ord-309386b960c9417bab8d846c925218c3
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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