Acetic Anhydride → 2-(Ethoxymethylidene)-3-oxobutanenitrile

HRID 1876757Notes

Reaction equation

HRID 1876757 reaction equation
[O:1]=[C:2]([CH3:6])[CH2:3][C:4]#[N:5].[CH2:7]([O:9][CH:10](OCC)OCC)[CH3:8].C(OC(=O)C)(=O)C>>[C:2]([C:3](=[CH:10][O:9][CH2:7][CH3:8])[C:4]#[N:5])(=[O:1])[CH3:6]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 755793-Oxobutyronitrile

Product 1

HCID 534170282-(Ethoxymethylidene)-3-oxobutanenitrile

Procedure

3-Oxo-butyronitrile (4.94 g, 60.9 mmol), triethylorthoformate (15.0 mL, 90.2 mmol), and acetic anhydride (0.3 mL, 2.7 mmol) were warmed to about 95-115° C. for about 1 hours, over which time a distillate was collected and discarded. After cooling the resultant mixture to room temperature, hexanes were added and a precipitate formed. The resultant mixture was filtered and the solids washed with hexanes, to yield the title compound as a solid.

Workup

  1. customwas collected
  2. additionhexanes were added
  3. customa precipitate formed
  4. filtrationThe resultant mixture was filtered
  5. washthe solids washed with hexanes

Sources & evidence

ORD record
ord-98d890f55a844821b07a45c64bbf7211
Source dataset
uspto-grants-2012_11
Patent number
US08309720B2

Reaction notes

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