Acetic Anhydride → α-(Acetyloxy)-α-methylcyclopropaneacetonitrile

HRID 1929805Notes

Reaction equation

HRID 1929805 reaction equation
[CH:1]1([C:4]([O:8][Si](C)(C)C)([CH3:7])[C:5]#[N:6])[CH2:3][CH2:2]1.[C:13](OC(=O)C)(=[O:15])[CH3:14]>C(#N)C.FC(F)(F)S([O-])(=O)=O.[Sc+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>[C:13]([O:8][C:4]([CH3:7])([CH:1]1[CH2:3][CH2:2]1)[C:5]#[N:6])(=[O:15])[CH3:14]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 588006α-Methyl-α-[(trimethylsilyl)oxy]cyclopropaneacetonitrile

Product 1

HCID 21109722α-(Acetyloxy)-α-methylcyclopropaneacetonitrileYield 87.5%

Reagents, catalysts & solvents 2

HCID 2734571Scandium(III) triflateCatalystHCID 6342AcetonitrileSolvent

Procedure

To a well stirred and ice-cooled solution of 2-cyclopropyl-2-trimethylsilanyloxy-propionitrile (188.5 g, 1.03 mol) in acetonitrile (1000 mL) was added acetic anhydride (194 mL, 2.06 mol) and scandium trifluoromethanesulfonate (5 g, 10.3 mmol). The temperature rose to ˜10° C. and stirring was continued for 15′ at room temperature. The solvent was evaporated in vacuo and the residue was distilled to yield 138 g of the title compound as colorless liquid, bp: 84-86° C./6 mbar.

Workup

  1. customrose to ˜10° C.
  2. stirringstirring
  3. customat room temperature
  4. customThe solvent was evaporated in vacuo
  5. distillationthe residue was distilled

Sources & evidence

ORD record
ord-43665291a7f949e8bef2c8d30872cc16
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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