Methyl 5-bromovalerate → Methyl 5-methoxypentanoate

HRID 964302Notes

Reaction equation

HRID 964302 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-44faca24adc74dfb95a7dee71dbb3b44
Source dataset
uspto-grants-1998_06
Patent number
US05767131

Reaction notes

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