Potassium Cyanide → Methyl 5-cyanopentanoate
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
Product 1
Reagents, catalysts & solvents 2
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
- temperaturethe mixture is refluxed overnight
- concentrationThe reaction mixture is concentrated to dryness
- additionTo the residue, 100 mL of EtOAc is added
- extractionto extract the product
- washThe organic is washed with water three times
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6793678113e5437799565c1d49dd7856
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08529882B2
Reaction notes
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