Pyridine → Methyl 4-Cyanobutanoate

HRID 970395Notes

Reaction equation

HRID 970395 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.CN([CH:10]=[O:11])C.[N:12]1C=C[CH:15]=[CH:14][CH:13]=1.CCOCC>C(#N)C>[C:13]([CH2:14][CH2:15][CH2:2][C:1]([O:11][CH3:10])=[O:5])#[N:12]

Participants

6

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 65578Oxalyl chloride

Product 1

HCID 13879654Methyl 4-Cyanobutanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6.2 15 ml of oxalyl chloride are added dropwise at from −2 to 0° to a solution of 15 ml of DMF in 300 ml of acetonitrile, and the mixture is stirred for a further 30 minutes. 23.25 g of “FA” are added dropwise at a maximum of 0°, and, after the mixture has been stirred for 15 minutes, 29 ml of pyridine are added dropwise. Ether is added, and the mixture is subjected to conventional work-up, giving 20 g of methyl 4-cyanobutyrate (“FB”) as an oil.

Workup

  1. addition23.25 g of “FA” are added dropwise at a maximum of 0°
  2. stirringafter the mixture has been stirred for 15 minutes

Sources & evidence

ORD record
ord-74fe4d1549614e17bae841dde04542ea
Source dataset
uspto-grants-2007_12
Patent number
US07312224B2

Reaction notes

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