Water → Methyl 5-azidopentanoate

HRID 396680Notes

Reaction equation

HRID 396680 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].[N-:10]=[N+:11]=[N-:12].[Na+].O>CO>[N:10]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7])=[N+:11]=[N-:12]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 79557Methyl 5-bromovalerate

Product 1

HCID 14562330Methyl 5-azidopentanoateYield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 5-bromovalerate (5.00 g, 25.6 mmol), NaN3 (3.33 g, 51.2 mmol) and 15 ml of water in 40 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 removal of solvent, methyl 5-azidovalerate (4.01 g, 99.7%) 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. customremoval of solvent

Sources & evidence

ORD record
ord-9f7dc07f46344e9b949383d0096ae4f5
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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