Hydrochloric Acid → HCID 53256645, compound

Participants

Reaction Steps

Into dimethylformamide (250 mL), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (10.0 g, 45.5 mmol) and 2-(2-bromoethoxy)tetrahydro-2H-pyran (10.0 g, 45.5 mmol) were dissolved, to which 60% sodium hydride in oil (2.98 g, 68.3 mmol) was added while cooling with ice, followed by stirring for three hours while cooling with ice, and further for 17 hours at room temperature. Ethyl acetate was then added, and excess hydrated sodium was neutralized with 1M hydrochloric acid. Further, water was added and the resulting solution was separated. The resulting organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-70:30, V/V) to give the desired title compound (13.3 g, yield 84%).

Provenance & Evidence