Acetic Anhydride → 2-(2-Ethyl-butyryl)-3-ethoxy-but-2-enenitrile

HRID 324374Notes

Reaction equation

HRID 324374 reaction equation
[CH2:1]([CH:3]([CH2:9][CH3:10])[C:4](=[O:8])[CH2:5][C:6]#[N:7])[CH3:2].[C:11]([O:14][C:15](=O)[CH3:16])(=O)[CH3:12].C(OCC)(OCC)(OCC)C>C(OCC)(=O)C.O>[CH2:1]([CH:3]([CH2:9][CH3:10])[C:4]([C:5](=[C:11]([O:14][CH2:15][CH3:16])[CH3:12])[C:6]#[N:7])=[O:8])[CH3:2]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 66221Triethyl orthoacetateHCID 235057484-Ethyl-3-oxohexanenitrile

Product 1

HCID 540497052-(2-Ethyl-butyryl)-3-ethoxy-but-2-enenitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-ethyl-3-oxo-hexanenitrile (1.013 g, 7.28 mmol), acetic anhydride (1.5 ml) and triethyl orthoacetate (1.240 g, 7.64 mmol) was heated to reflux overnight. The reaction mixture was taken up in ethyl acetate and water. The brine and the ethyl acetate layer were separated. The organic layer was dried and concentrated to give 1.262 g of dry oil which was used directly for the next reaction. 1H NMR (CDCl3): 0.8-1.0(m,6H), 1.44(t,3H), 1.4-1.8(m,4H), 2.61(s,3H), 3.03(m,1H), 4.28(q, 2H)ppm.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customThe brine and the ethyl acetate layer were separated
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b47ea97e79fb4d2b90c1f65e63cfc237
Source dataset
uspto-grants-2001_04
Patent number
US06218397B1

Reaction notes

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