1,2-Dimethoxyethane → 4-(2-Cyanoethyl)benzonitrile

HRID 5941

Reaction equation

HRID 5941 reaction equation
CC(C)([O-])C.[K+].COCCOC.[C:13]([C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1)(=O)[CH3:14].C1(C)C=CC(S([CH2:33][N+:34]#[C-])(=O)=O)=CC=1>C(O)C>[C:20]([C:19]1[CH:22]=[CH:23][C:16]([CH2:13][CH2:14][C:33]#[N:34])=[CH:17][CH:18]=1)#[N:21]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 740444'-CyanoacetophenoneHCID 161915Tosylmethyl isocyanideHCID 23665647Potassium tert-butoxide

Product 1

HCID 2730084-(2-Cyanoethyl)benzonitrileYield 70.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.40 g (1.25 mmole) of potassium tert-butoxide was added to a 17 ml ethylene glycol dimethyl ether solution containing 0.73 g (5 mmole) of 4-acetylbenzonitrile, 0.5 ml of ethanol and 1.27 g (6.5 mmole) of p-toluenesulfonylmethylisocyanide under ice-cooling; then the mixture was stirred at room temperature for 0.5 hour and then at 40° C. for an additional hour. After the reaction mixture was cooled by allowing to stand at room temperature, it was filtered under reduced pressure and the filtrate was purified by silica gel chromatography to obtain 0.55 g (yield: 70.4 %) of 2-(4-cyanophenyl)ethylcyanide.

Workup

  1. temperaturecooling
  2. waitat 40° C. for an additional hour
  3. temperatureAfter the reaction mixture was cooled
  4. customto stand at room temperature
  5. filtrationit was filtered under reduced pressure
  6. customthe filtrate was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5feff57a661c408cb8eed94f0365db77
Source dataset
uspto-grants-1993_09
Patent number
US05246958

Linked notes

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