1-(((6-(Methoxycarbonyl)-5-oxononan-4-yl)oxy)carbonyl)cyclopropane-1-carboxylic Acid

Here, we first report the 2 & PRIME;-acyloxy-1,3-dicarbonyl compound construction in a three-component oxidative reaction of alkyl ketene dimer with cyclic diacyl peroxide and trimethyl orthoformate. The discovered synthesis allows us to form 2 & PRIME;-functionalized 1,3-dicarbonyl compounds instead of the common 2-functionalized moiety. The reaction between 4-butylidene-3-propyloxetan-2-one and cyclopropyl malonoyl peroxide proceeds in the presence of trifluoroacetic acid and trimethyl orthoformate at 120 & DEG;C for 1 h. The synthesized compound was characterized by NMR spectroscopy, mass spectrometry, and IR spectroscopy.

Automated summary

We have reported a three-component oxidative reaction for the construction of 2'-acyloxy-1,3-dicarbonyl compounds using alkyl ketene dimer, cyclic diacyl peroxide, and trimethyl orthoformate. This synthesis allows the formation of 2'-functionalized 1,3-dicarbonyl compounds instead of the commonly found 2-functionalized moiety. The reaction was performed between 4-butylidene-3-propyloxetan-2-one and cyclopropyl malonoyl peroxide in the presence of trifluoroacetic acid and trimethyl orthoformate at 120°C for 1 hour. The synthesized compound was characterized using NMR spectroscopy, mass spectrometry, and IR spectroscopy.