1618101-91-9

Upstream product

• 100-59-4 phenylmagnesium chloride 
• 40877-19-8 4-chloro-1-(4-methoxyphenyl)butan-1-one 
• 591-51-5 phenyllithium 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 939-52-6 4-chloro-1-phenylbutan-1-one 
• 699-19-4 4-methoxyphenylmagnesium chloride 

Downstream Products

• 1618101-88-4 5-methoxy-2-(2-phenyltetrahydrofuran-2-yl)benzaldehyde 
• 1618101-89-5 2-[2-(4-methoxyphenyl)tetrahydrofuran-2-yl]benzaldehyde 

Relevant academic research and scientific papers

Water opens the door to organolithiums and Grignard reagents: Exploring and comparing the reactivity of highly polar organometallic compounds in unconventional reaction media towards the synthesis of tetrahydrofurans

It has always been a firm conviction of the scientific community that the employment of both anhydrous conditions and water-free reaction media is required for the successful handling of organometallic compounds with highly polarised metal-carbon bonds. Herein, we describe how, under heterogeneous conditions, Grignard and organolithium reagents can smoothly undergo nucleophilic additions to γ-chloroketones, on the way to 2,2-disubstituted tetrahydrofurans, "on water", competitively with protonolysis, under batch conditions, at room temperature and under air. The reactivity of the above organometallic reagents has also been investigated in conventional anhydrous organic solvents and in bio-based eutectic and low melting mixtures for comparison. The scope and limitations of this kind of reaction are discussed.

Regioselective desymmetrization of diaryltetrahydrofurans via directed ortho-lithiation: An unexpected help from green chemistry

An efficient functionalization of diaryltetrahydrofurans via a regioselective THF-directed ortho-lithiation is first described. This reaction can be successfully carried out in cyclopentyl methyl ether as a greener alternative to Et2O, with better results in terms of yield and selectivity and, surprisingly, also in protic eutectic mixtures competitively with protonolysis.