Water → Methyl 5-azidopentanoate

HRID 322185Notes

Reaction equation

HRID 322185 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-80567bd781fe4140ab371cb5562bbea4
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

Loading…