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The lithium enolate (18) of methyl 3-(dimethylamino)propionate (17) has been developed as a synthetic equivalent of the -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 -methylene lactones.
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