Pentanedioic acid, 2,4-diacetyl-, diethyl ester synthesis
- Product Name:Pentanedioic acid, 2,4-diacetyl-, diethyl ester
- CAS Number:67079-26-9
- Molecular formula:C13H20O6
- Molecular Weight:272.29
Yield:67079-26-9 30%
Reaction Conditions:
with dipotassium peroxodisulfate in acetonitrile at 60; for 5 h;Sealed tube;
Steps:
General procedure for the methylene-bridged bis-1,3-dicarbonyl compounds 3a-t
General procedure: K2S2O8 (270mg, 1.0mmol), dibenzoylmethane 1a (112mg, 0.5mmol) were added to a solution of N,N,N′,N′-tetramethylethylenediamine 2a (116mg, 1.0mmol) in CH3CN (2.0mL), the reaction mixture was stirred in a sealed tube at 60°C for 5h. The reaction was monitored by TLC. Once the reaction was completed, the reaction mixture was treated with H2O (5.0mL) and EtOAc (8.0mL). The organic and aqueous layers were then separated, and the aqueous layer was extracted with EtOAc (3×8mL). The combined organic extracts were dried (Na2SO4), then the solvent was removed under reduced pressure and the remaining residue was purified by column chromatography. Compound 3a (110.4mg, 96% yield) was obtained as a light yellow powder.
References:
Wang, Xiaohu;Wang, Yi;Yuan, Yu;Xing, Chun-Hui [Tetrahedron,2014,vol. 70,# 12,p. 2195 - 2202]
