Acetonitrile → HCID 57672017, compound

HRID 657629Notes

Reaction equation

HRID 657629 reaction equation
[C-:1]#[N:2].[K+].CS(O[C@@H:9]([CH2:11][C@H:12](OS(C)(=O)=O)[CH3:13])[CH3:10])(=O)=O.[C:19](#[N:21])C>>[CH3:10][C@@H:9]([CH2:11][C@H:12]([CH3:13])[C:19]#[N:21])[C:1]#[N:2]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 9032Potassium CyanideHCID 10539266HCID 10539266, compound

Product 1

HCID 57672017HCID 57672017, compound

Procedure

A suspension of potassium cyanide (36 g) in a solution of (2R,4R)-2,4-pentanediol dimethanesulfonate (36 g) dissolved in acetonitrile (77 mL) is stirred overnight under reflux. The mixture is partitioned between dichloromethane (200 mL) and water (150 mL). The organic layer is extracted six times with dichloromethane. The combined organic extracts are dried over magnesium sulphate, concentrated under reduced pressure and purified by chromatography over silica gel using a gradient heptane/ethyl acetate from 4/1 to 2/1 to give 8.3 g of (2S,4S)-2,4-dimethylpentanedinitrile as a yellow solid used without further purification.

Workup

  1. temperatureunder reflux
  2. customThe mixture is partitioned between dichloromethane (200 mL) and water (150 mL)
  3. extractionThe organic layer is extracted six times with dichloromethane
  4. dry with materialThe combined organic extracts are dried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. custompurified by chromatography over silica gel using a gradient heptane/ethyl acetate from 4/1 to 2/1

Sources & evidence

ORD record
ord-b4887e938f774447acad556945df5b23
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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