Dimethyl Sulfate → 3-Methoxy glutaronitrile
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
Product 1
Reagents, catalysts & solvents 1
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
- additionwas slowly dropped
- additionwas slowly added dropwise
- stirringAfter stirring at room temperature for 6 hours
- extractionthe reactant was extracted
- 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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