diethyl 2-acetamido-2-(2-cyanoethyl)propanedioate synthesis
- Product Name:diethyl 2-acetamido-2-(2-cyanoethyl)propanedioate
- CAS Number:5440-42-6
- Molecular formula:C12H18N2O5
- Molecular Weight:270.28
Yield:5440-42-6 83%
Reaction Conditions:
with tetrabutylammomium bromide;potassium carbonate in tetrahydrofuran;Reflux;
Steps:
ω-Cyanoalkylacetamidomalonic esters (3).
General procedure: A mixture of 4.3 g (20 mmol) of acetamidomalonic ester, 22 mol of the corresponding ω-bromoalkylnitrile 4, 8.3 g (60 mmol) of finely dispersed K2CO3, and 0.1 g of tetrabutylammonium bromide in 15-20 mL of tetrahydrofuran was stirred under reflux for 13-18 h. The reaction progress was monitored by TLC. After the reaction completed, the mixture was filtered, and the filtrate was evaporated in a vacuum. The residue was poured into a mixture of cold water (30 mL) and ice. The aqueous layer was neutralized with 1 N solution of HCl to pH ~ 7 and extracted with ethylacetate (3×30 mL). The combined organic extract was dried with magnesium sulfate and evaporated in avacuum. The residue was crystallized from diethyl or petroleum ether.
References:
Ragulin [Russian Journal of General Chemistry,2018,vol. 88,# 5,p. 1045 - 1048][Zh. Obshch. Khim.,2018,vol. 88,# 5,p. 862 - 865,4]
