Beilstein J. Org. Chem.2014,10, 1365–1371, doi:10.3762/bjoc.10.139
synthetic route to prepare 1 using cheap and commercially available diethyl2-acetamidomalonate (4) and propargyl alcohol. The desired product 1 was obtained via alkylation of malonate 4 with propargyl tosylate followed by a one-pot four-step sequence of hydrolysis, decarboxylation, diazotization and
hydroxylation of propargylic malonate 5 without work-up of any intermediate.
Keywords: alkylation; ‘click’ chemistry; ‘clickable’ polylactide; decomposition; diethyl2-acetamidomalonate; 2-hydroxy-4-pentynoic acid; one-pot; optimization; propargyl bromide; propargyl tosylate; safe and economical; Introduction
economical and safe procedure using diethyl2-acetamidomalonate (4) and propargyl alcohol as starting materials to synthesize 1. The synthesis was completed via alkylation of malonate 4 with propargyl tosylate followed by a one-pot four-step sequence of hydrolysis, decarboxylation, diazotization and
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Graphical Abstract
Scheme 1:
Synthesis of 2-hydroxy-4-pentynoic acid (1).