Methyl 5-bromovalerate → Methyl 5-methoxypentanoate

HRID 396696Notes

Reaction equation

HRID 396696 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].[CH3:10][O-:11].[Na+]>CO>[CH3:10][O:11][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 79557Methyl 5-bromovalerateHCID 10942334Sodium Methoxide

Product 1

HCID 542362Methyl 5-methoxypentanoateYield 97.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 5-bromovalerate (10.0 g, 51.3 mmol), NaOMe (12.3 ml of 25% solution, 53.8 mmol) in 100 ml of MeOH was refluxed for 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 (100 ml). After drying (Na2SO4) and evaporation of solvent, methyl 5-methoxyvalerate (7.33 g, 97.8%) 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 (100 ml)
  5. customAfter drying
  6. custom(Na2SO4) and evaporation of solvent

Sources & evidence

ORD record
ord-8e84b30941c74fc3ace4e024b18dadc9
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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