1978•Chemical and Pharmaceutical BulletinOpen access
Reaction of ethyl 4-halo-3-oxobutanoate with diethyl malonate, methyl cyanoacetate, and malononitrile.
Tetsuzo Kato, Hitoshi Kimura, Ken‐ichi Tanji
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Abstract
Ethyl 4-bromo (and chloro)-3-oxobutanoate (1 and 2) reacts with diethyl malonate in the presence of sodium hydride to give diethyl 5-ethoxycarbonyl-3-oxohexanedioate (3) and diethyl 5-carboxy-3-oxohexanedioate (4). Similarly, reaction of the haloester (1, 2) with methyl cyanoacetate gives 1-ethyl methyl 5-cyano-3-oxohexanedioate (6) and 1-ethyl hydrogen 5-cyano-3-oxohexanedioate (7). On the other hand, 1 reacts with malononitrile in the presence of triethylamine to give ethyl 5-amino-4-cyanofuran-2-acetate (8) and ethyl 3-amino-2, 4, 4-tricyano-2-cyclopenten-1-ylideneacetate (9).
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