104643-76-7

Basic information

• Product Name: diethyl (1-ethyl-2-methyl-propyl)malonate
• Synonyms: diethyl (1-ethyl-2-methyl-propyl)malonate
• CAS NO: 104643-76-7
• Molecular Weight: 244.331
• Mol File: 104643-76-7.mol

Chemical Properties

• CAS DataBase Reference: diethyl (1-ethyl-2-methyl-propyl)malonate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl (1-ethyl-2-methyl-propyl)malonate(104643-76-7)
• EPA Substance Registry System: diethyl (1-ethyl-2-methyl-propyl)malonate(104643-76-7)

Safety Data

• Hazardous Substances Data: 104643-76-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Diethyl (1-ethyl-2-methyl-propyl)malonate is used as a synthetic intermediate for the preparation of various organic compounds. Its reactivity allows for the formation of new chemical bonds and the construction of complex molecular structures.
Used in Conjugate Addition Reactions:
In the field of organic chemistry, diethyl (1-ethyl-2-methyl-propyl)malonate is used as a substrate for conjugate addition reactions involving dialkylaluminum chlorides. This application takes advantage of the compound's ability to form new carbon-carbon bonds, facilitating the synthesis of more complex molecules.
Used in Cyclopentane Annelation Reactions:
Diethyl (1-ethyl-2-methyl-propyl)malonate is also utilized in cyclopentane annelation reactions, where it serves as a key component in the formation of cyclopentane rings. This process is crucial for the synthesis of various pharmaceuticals, agrochemicals, and other specialty chemicals that contain cyclopentane moieties.

Upstream product

• 16783-05-4 diethyl 2,2-dimethyl cyclopropane 1,1-dicarboxylate 
• 563-43-9 ethylaluminum dichloride 
• 5652-68-6 diethyl 2-(2-methylpropylidene)malonate 
• 96-10-6 diethylaluminium chloride 

Relevant articles and documents

Mixed Dialkylaluminum Chlorides and Mixed Trimethylorganoaluminates in Chemoselective 1,4 Addition Reactions to Alkylidene Malonic Acid Diethyl Ester

Mixed alkyl-methyl- and aryl-methylorganoaluminum chlorides 6 were formed by reaction of methylaluminum dichloride with organolithium or Grignard compounds and used for chemoselective 1,4 addition of higher alkyl, aryl, alkenyl and alkinyl groups to alkylidine malonic esters 1 and 2. As an alternative, mixed trimethylorganoaluminates 7 can also be applied for these Michael addition reactions. For conjugate addition of alkenyl groups to alkylidene malonates 1 and 2, alkenyl diisopropylalanes 10 obtained from alkynes and diisopropylaluminum hydride proved the most efficient reagents. Using these novel mixed organoaluminum compounds, β-branched malonic (carboxylic) acid derivatives 3c, 8, 9 and 11 were obtained in good yields. The method offers a general access to β-branched carboxylic derivatives of quite diverse structure not dependent on the commercial availability of the organoluminum chlorides.

Conjugate addition of dialkylaluminum chlorides to alkylidenemalonic acid derivatives

Complete regioselectivity is achieved in conjugate addition reactions of dialkylaluminum chlorides with alkylidenemalonic esters, alkylidenecyanoacetates, and alkylidenemalonodinitrile to give β-branched carboxylic acid derivatives. Sterically demanding products containing quaternary carbon atoms are obtained in good yields. In the case of diethylaluminum chloride, accompanying reductions of the substrates can be suppressed by application of boron trifluoride as an assisting Lewis acid.

EtAlCl2-Catalyzed Reactions of Alkenes with Electrophillic Cyclopropanes. A New Cyclopentane Annelation Reaction

Treatment of 1,1-di-, tri-, and tetrasubstituted alkenes with diethyl cyclopropane-1,1-dicarboxylate (1) and 2 equiv of EtAlCl2 gives zwitterions which collapse to cyclopentanedicarboxylates in good to excellent yield.This reaction provides a general procedure for the annelation of cyclopentanes to alkenes.The intermediate zwitterions undergo the 1,2-hydride and -methyl shifts characteristic of carbocations, although these side reactions are generally minor.Diethyl 2-methylcyclopropane-1,1-dicarboxylate (38) reacts similarly with alkenes at the more substituted carbon of 38 to give 3-methylcyclopentane-1,1-dicarboxylates.Diethyl 2,2-dimethylcyclopropane-1,1-dicarboxylate (46) rearranges in the presence of EtAlCl2 to diethyl isobutylidenemalonate, which reacts with alkenes and is reduced by EtAlCl2.The intramolecular Lewis acid induced addition of alkenes to cyclopropanedicarboxylate esters occurs analogously.