Potassium Cyanide → Methyl 5-cyanopentanoate

HRID 1161946Notes

Reaction equation

HRID 1161946 reaction equation
[C-:1]#[N:2].[K+].Br[CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10]>O.CO>[C:1]([CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])#[N:2]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 79557Methyl 5-bromovalerate

Product 1

HCID 554130Methyl 5-cyanopentanoateYield 74.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Potassium Cyanide (4 g, 61.44 mmol) is dissolved in 70 mL water and 200 mL methanol. To the solution 10 g (51.2 mmol) of methyl 5-bromopentanoate is added and the mixture is refluxed overnight. The reaction mixture is concentrated to dryness. To the residue, 100 mL of EtOAc is added to extract the product. The organic is washed with water three times, dried and concentrated to yield 5.37 g (74%) of methyl 5-cyanopentanoate as an oil.

Workup

  1. temperaturethe mixture is refluxed overnight
  2. concentrationThe reaction mixture is concentrated to dryness
  3. additionTo the residue, 100 mL of EtOAc is added
  4. extractionto extract the product
  5. washThe organic is washed with water three times
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c6d8ee6ee3d94fdb93591967f5e2bd3f
Source dataset
uspto-grants-2010_10
Patent number
US07820671B2

Reaction notes

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