69637-62-3

Upstream product

• 3853-06-3 methyl 3-(dimethylamino)propionate 
• 1521-51-3 rac-3-bromocyclohexene 

Downstream Products

• 69637-65-6 (2-Cyclohex-2-enyl-2-methoxycarbonyl-ethyl)-trimethyl-ammonium; iodide 
• 16822-06-3 cis-3-methylenehexahydrobenzofuran-2-one 
• 60916-75-8 (3aR,7aR)-3-Methylene-3a,4,5,7a-tetrahydro-3H-benzofuran-2-one 
• 69637-66-7 2-(2-cyclohexenyl)-2-propenoic methylester 
• 54109-55-6 2-Cyclohex-2-enyl-acrylic acid 

Relevant academic research and scientific papers

β-Amino Ester Enolate as an Acrylate Anion Equivalent for the Synthesis of α-Methylene Esters, Acids, and Lactones

The lithium enolate (18) of methyl 3-(dimethylamino)propionate (17) has been developed as a synthetic equivalent of the α-anion (15) of acrylic acid.The enolate, obtained by treatment of the free ester (17) with lithium diisopropylamide, may be alkylated with a variety of alkyl halides to give products which may be considered to be protected acrylate esters.Unmasking is accomplished by quaternization with methyl iodide followed by DBN-induced elimination to give the free acrylates.The products derived from allylic halides may conveniently be converted into α-methylene lactones.

USE OF METHYL 3-(N,N-DIMETHYLAMINO)PROPIONATE AS A SYNTHON FOR THE CONSTRUCTION OF α-METHYLENE γ-BUTYROLACTONES

The lithium enolate of methyl 3-(N,N-dimethylamino)propionate reacts with allylic halides to give alkylation products which may be converted into α-methylene γ-butyrolactones by a reaction sequence which includes iodolactonization among other simple steps.