Dimethyl Sulfoxide → 3,3-Diethoxypropiononitrile

HRID 1196751Notes

Reaction equation

HRID 1196751 reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5]Br)[CH3:2].[C-:10]#[N:11].[Na+].CS(C)=O>O>[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][C:10]#[N:11])[CH3:2]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 748513,3-Diethoxypropiononitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 8 g of bromo-acetaldehyde diethyl-acetal, 3 g of sodium-cyanide and 20 ml of dimethyl-sulfoxide is admixed at a temperature of 80° C. for 5 hours. The reaction mixture is poured on 80 ml of water, then twice extracted with 50 ml of chloroform. The chloroform extract is washed twice with 30 ml of water, dried on magnesium sulfate, then distilled in vacuo.

Workup

  1. extractiontwice extracted with 50 ml of chloroform
  2. extractionThe chloroform extract
  3. washis washed twice with 30 ml of water
  4. customdried on magnesium sulfate
  5. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-b84da5d5dbfa45d0a46ae7e2a8b4fbec
Source dataset
uspto-grants-1992_05
Patent number
US05116402

Reaction notes

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