67498-38-8

Upstream product

• 13206-46-7 2-bromo-2-methylpropanal 
• 996-82-7 sodium diethylmalonate 
• 67498-36-6 ethyl 4-bromo-2-carbethoxy-4-methyl-2-pentenoate 
• 130382-38-6 diethyl 2-(2-chloro-2-methylpropylidene)malonate 
• 82024-35-9 ethyl methyl (E)-2-bromo-2-methylpropylidenemalonate 
• 82024-40-6 methyl hydrogen (Z)-2-bromo-2-methylpropylidenemalonate 
• 5652-68-6 diethyl 2-(2-methylpropylidene)malonate 
• 105-53-3 diethyl malonate 

Downstream Products

• 1421959-27-4 (3S,4R)-ethyl 5,5-dimethyl-2-oxo-4-(2-oxo-2-phenylethyl)tetrahydrofuran-3-carboxylate 
• 1421959-28-5 (3S,4R)-ethyl 4-(2-(4-fluorophenyl)-2-oxoethyl)-5,5-dimethyl-2-oxotetrahydrofuran-3-carboxylate 
• 1421959-29-6 (3S,4R)-ethyl 4-(2-(4-chlorophenyl)-2-oxoethyl)-5,5-dimethyl-2-oxotetrahydrofuran-3-carboxylate 
• 1421959-30-9 (3S,4R)-ethyl 4-(2-(4-bromophenyl)-2-oxoethyl)-5,5-dimethyl-2-oxotetrahydrofuran-3-carboxylate 
• 1421959-31-0 (3S,4R)-ethyl 5,5-dimethyl-4-(2-(4-nitrophenyl)-2-oxoethyl)-2-oxotetrahydrofuran-3-carboxylate 
• 1421959-32-1 (3S,4R)-ethyl 5,5-dimethyl-2-oxo-4-(2-oxo-2-p-tolylethyl)tetrahydrofuran-3-carboxylate 
• 1421959-33-2 (3S,4R)-ethyl 4-(2-(3-chlorophenyl)-2-oxoethyl)-5,5-dimethyl-2-oxotetrahydrofuran-3-carboxylate 

Relevant academic research and scientific papers

A reactive lactonic dienophile - 3-carbethoxy-5,5-dimethyl-2(5H)-furanone. Application to the synthesis of a monoterpenoid lactone

In contrast to the low dienophilicity generally observed for α,β-unsaturated lactones, the title compound 2 is shown to be a reactive dienophile.Under stannic chloride catalysis, it undergoes Diels-Alder reaction regio- and stereoselectively with a variety of dienes at room temperature.The synthesis of (+/-)-o-mentha-1,3-dien-1->8-olide (20) has been achieved by a two-step sequence using lactone ester 2.Addition of 2 to 1-acetoxy-1,3-butadiene afforded epimeric acetoxy lactones 12 and 13 which were converted to the monoterpenoid lactone 20 by treatment with lithium iodide dihydrate in collidine.

An efficient organocatalytic enantioselective Michael addition of aryl methyl ketones with 2-furanones: Highly functionalized chiral 3,4-substituted lactones

The efficient asymmetric Michael addition reactions of aryl methyl ketones with 2-furanones were catalyzed by a simple and commercially available chiral 1,2-diphenyl-1,2-ethanediamine and p-TSA·H2O as cocatalyst with good yields (up to 95%) and excellent enantioselectivities (up to >99% ee). A bi-functional catalytic mechanism for the reaction was proposed.

REFORMATSKY REACTION WITH DIETHYL 2-(2-CHLORO-2-METHYLPROPYLIDENE)MALONATE. ANALYSIS OF THE PRODUCTS BY PMR SPECTROSCOPY

The reaction of diethyl 2-(2-chloro-2-methylpropylidene)malonate with zinc gives an ambident organozinc compound.With electrophilic reagents the latter gives the products from γ and α attack, i.e., derivatives of alkylidene- and alkenylmalonic acid with a preference for the latter.

On the Reaction of the Half Esters of 2-Methylpropylidene Malonic Acid with N-Bromosuccinimide. Preparation of Ethyl Methyl (E)-2-Bromo-2-methylpropylidenemalonate

In addition to normal allylic bromination, a secondary reaction, bromodecarboxylation, takes place when the half esters of 2-methylpropylidene malonic acid react with N-bromosuccinimide (NBS).Of the two isomeric half esters the one having the carboxyl group on the same side as the bromoisopropyl group (E-isomer) undergoes this secondary reaction most easily, while there are strong indications that the Z isomer rearranges to the E isomer before reaction.The preparation of the isomerically pure ethyl methyl (E)-2-bromo-2-methylpropylidenemalonate is described.