Here we report a new synthetic route to substituted 4-vinyl chromanes. The key synthetic step involves electrophilic activation of propargyl silanes 2 followed by tandem 1,2-silyl shift – Friedel–Crafts cyclization. Propargyl silanes 2 can be obtained from commercially available pent-4-yn-1-ol (1) in 3 steps: O-silylation, retro-Brook rearrangement under Schlosser conditions and modified Mitsunobu reaction with corresponding phenols. Additionally, halogen atom moiety can be introduced in the terminal alkyne position via silver(I) catalysis. Resulting propargyl silanes 2 in the presence of strong Brønsted acids undergo cyclization to yield vinyl chrormanes 3, whereas E-selective haloalkyne cyclization leads to stereodefined olefin side chain.