Dimethyl Sulfate → 3-Methoxy glutaronitrile

HRID 1849949Notes

Reaction equation

HRID 1849949 reaction equation
[H-].[Na+].[OH:3][CH:4]([CH2:8][C:9]#[N:10])[CH2:5][C:6]#[N:7].S(OC)(O[CH3:15])(=O)=O>O1CCCC1>[CH3:15][O:3][CH:4]([CH2:8][C:9]#[N:10])[CH2:5][C:6]#[N:7]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 3617621,3-Dicyano-2-propanol

Product 1

HCID 155010063-Methoxy glutaronitrileYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Into a tetrahydrofuran solution, 0.7 g of sodium hydride was added. After cooling to 0° C., 3 g of 3-hydroxyglutaronitrile dissolved in a tetrahydrofuran solvent was slowly dropped. After completing the dropping, dimethyl sulfate was slowly added dropwise and stirred at 0° C. for 15 minutes. After stirring at room temperature for 6 hours, the reactant was extracted using water and dichloromethane and distilled under a reduced pressure to obtain 3-methoxy glutaronitrile (yield 82%).

Workup

  1. additionwas slowly dropped
  2. additionwas slowly added dropwise
  3. stirringAfter stirring at room temperature for 6 hours
  4. extractionthe reactant was extracted
  5. distillationdistilled under a reduced pressure

Sources & evidence

ORD record
ord-6663b6a438744311b993b5b0db71a312
Source dataset
uspto-grants-2015_02
Patent number
US08956769B2

Reaction notes

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