Acetonitrile → 3-(1-Methylcyclopropyl)-3-oxopropanenitrile

HRID 615524Notes

Reaction equation

HRID 615524 reaction equation
[C:1](#[N:3])[CH3:2].[CH3:4][C:5]1([C:8](OC)=[O:9])[CH2:7][CH2:6]1.[H-].[Na+]>O1CCCC1>[CH3:4][C:5]1([C:8]([CH2:2][C:1]#[N:3])=[O:9])[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 543995Methyl 1-methylcyclopropane-1-carboxylate

Product 1

HCID 133930463-(1-Methylcyclopropyl)-3-oxopropanenitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 61.1 g of acetonitrile and 108.3 g of methyl 1-methylcyclopropanecarboxylate was added drop-by-drop over a one-hour period to a stirred, refluxing mixture of 35.8 g of sodium hydride and 650 ml of tetrahydrofuran. The resulting mixture was stirred and refluxed for a further 18 hours, then most of the solvent was evaporated in a rotary evaporator. The residue was dissolved in 1 liter of water, and the solution was acidified with hydrochloric acid and extracted with ether. The extract was dried (MgSO4) and concentrated. The residue, a liquid, was fractionally distilled to give (1-methylcyclopropylcarbonyl)acetonitrile (D) as a colorless oil which crystallized on standing, m.p.: 32°-33° C.

Workup

  1. additionwas added drop-by-drop over a one-hour period to a stirred
  2. temperaturerefluxing
  3. temperaturerefluxed for a further 18 hours
  4. custommost of the solvent was evaporated in a rotary evaporator
  5. dissolutionThe residue was dissolved in 1 liter of water
  6. extractionextracted with ether
  7. dry with materialThe extract was dried (MgSO4)
  8. concentrationconcentrated
  9. distillationThe residue, a liquid, was fractionally distilled

Sources & evidence

ORD record
ord-5007759cf3dd43fe9cdb287888f70db2
Source dataset
uspto-grants-1985_02
Patent number
US04500345

Reaction notes

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