The synthesis of the SiHDs (Scheme 2) began with the treatment of 3-bromo aniline with ethyl iodide to yield 3-bromo-N,N-diethylaniline 2. Next, a Vilsmeier-Haack reaction was performed to obtain the paraformylated intermediate 3 in 48% yield. Protection of the aldehyde with ethylene glycol under acidic conditions afforded acetal 4 with 59% conversion. In parallel, the acetal-protected vinyl bromide building block 5 was prepared in 26% yield over 2-steps. With 4 and 5 in hand, we screened conditions to obtain dialdehyde 6. For instance, we activated one component (4 or 5) with n-butyllithium, followed by the sequential addition of dichlorodimethylsilane and the second component after lithium halogen exchange. Moreover, we explored activation of both compounds in one-pot at different ratios prior to the addition of the silane. We determined the most reproducible, scalable, and high yielding combination was the simultaneous activation of 4 and 5 (at a 1:1 molar ratio), which gave 6 in 34% upon acid-mediated deprotection.