Hydrochloric Acid → 5-Cyanoacetyl-furan-2-carbonitrile

HRID 1356172Notes

Reaction equation

HRID 1356172 reaction equation
[H-].[Na+].[C:3](#[N:5])[CH3:4].C[O:7][C:8]([C:10]1[O:11][C:12]([C:15]#[N:16])=[CH:13][CH:14]=1)=O.Cl>C1COCC1>[C:3]([CH2:4][C:8]([C:10]1[O:11][C:12]([C:15]#[N:16])=[CH:13][CH:14]=1)=[O:7])#[N:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 13011707Methyl 5-cyanofuran-2-carboxylate

Product 1

HCID 185075555-Cyanoacetyl-furan-2-carbonitrileYield 43.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 1,67 g (41.7 mmol, 60% dispersion in mineral oil) sodium hydride in a 2-necked flask fitted with a reflux condenser was added dropwise 150 ml THF and the mixture was then heated to reflux. A solution of 1.0 ml (208 mmol) acetonitrile and 6.30 g (41.7 mmol) 5-cyano-furan-2-carboxylic acid methyl ester in 100 ml dry THF was added dropwise and the reaction mixture heated at reflux for 4 hours. The reaction mixture was then cannulated into a rapidly stirred solution of 1M hydrochloric acid at 0° C. The mixture was extracted three times with ethyl acetate and the combined organic phases dried over sodium sulfate and concentrated in vacuo. Chromatography (ethyl acetate/hexane 1/1) afforded 2.90 g (43%) 5-cyanoacetyl-furan-2-carbonitrile as an orange oil. EI-MS m/e (%): 160 (M+, 19), 120 ([M—CH2CN]+, 100).

Workup

  1. temperaturethe mixture was then heated to reflux
  2. temperaturethe reaction mixture heated
  3. temperatureat reflux for 4 hours
  4. extractionThe mixture was extracted three times with ethyl acetate
  5. dry with materialthe combined organic phases dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be7e99a5def24731823b34f86494555c
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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