The classic Henry Reaction, a nitroaldol condensation, is notoriously problematic. It is driven by a strong base, whose presence initiates unwanted side reactions and results in poor yields. This work explores the synthesis of aminosilane that, when attached to commercially available silica gel, would enable the nitroaldol condensation for alpha-branched and linear aldehydes. The presence of the aminosilane minimizes side reactions, shortens reaction times, eliminates solvent use, and simplifies product isolation as compared to literature yields of nitroalcohols. This research also explores the regeneration of the aminosilane, thus proposing a simpler, greener method for nitroaldol condensations.