Abstract1 Tin(II) chloride‐mediated Barbier‐type coupling of ethyl glyoxylate with 2,3‐dibromopropene followed by Simmons–Smith cyclopropanation and subsequent Dess–Martin oxidation, afforded ethyl 3‐(1‐bromocycloprop‐1‐yl)‐2‐oxopropionate (5), a stable precursor of ethyl cyclopropylidenepyruvate (1j), in good overall yield (65 %), even on a multi‐gram scale. The potentially rich chemistry of this novel cyclopropyl building block was illustrated by some basic transformations such as Michael additions of N‐, S‐, O‐ and C‐nucleophiles (10–91 % yields), Diels–Alder reactions with cyclopentadiene (65 %) and 2,3‐dimethylbuta‐1,3‐diene (66 %) as well as [4+2] cycloadditions across the enone moiety of 1j (hetero‐Diels–Alder reactions) with furan and enol ethers (65–79 %), thus opening up a ready access to a wide range of new variously functionalized cyclopropane derivatives.