Ethyl cyanoacetate → 2-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester

HRID 1297667Notes

Reaction equation

HRID 1297667 reaction equation
[CH:1]([O:8]CC)([O:5][CH2:6][CH3:7])OCC.[C:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=O)#[N:12]>C(OC(=O)C)(=O)C>[C:11]([C:13](=[CH:14][O:16][CH2:17][CH3:18])[C:1]([O:5][CH2:6][CH3:7])=[O:8])#[N:12]

Participants

4

Reactant 2

HCID 7764Ethyl cyanoacetateHCID 31214Ethyl orthoformate

Product 1

HCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterYield 84.2%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
155 °C

Procedure

The mixture of triethyl orthoformate (33.3 mL, 0.2 mol) and ethyl cyanoacetate (21.3 mL, 0.2 mol) in acetic anhydride (80 mL) was heated at 150-160° C. for 5 h. After cooling to room temperature, the solvent was removed under reduced pressure to give ethyl 2-cyano-3-ethoxyacrylate as a yellow solid (28.5 g, 84%).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-74a03181e8c3440b96c32c04a4cf413d
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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