Ethanol → HCID 59674890, compound

Participants

Reaction Steps

The tert-butyl 4-{[(trifluoromethyl)sulfonyl]oxy}-3,6-dihydropyridine-1(2H)-carboxylate (6.42 g, 9.23 mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 4.69 g, 21.3 mmol, and tetrakis(triphenylphosphine)palladium(0) (200 mg, 0.17 mmol) were mixed in dioxane (20 mL), ethanol (10 mL) and 2 M aqueous sodium carbonate (5.0 mL). The solution was refluxed for 4 hours, cooled to room temperature, and poured into ethyl acetate (150 mL). The solution was extracted with 1N aqueous hydrochloric acid (2×100 mL), filtered through celite, extracted with saturated aqueous sodium bicarbonate (2×100 mL), and extracted with saturated with saturated aqueous ammonium chloride (2×100 mL). The solution was dried over sodium sulfate, vacuum filtered through a bed of silica gel and solvent removed at reduced pressure to afford a red oil. The tert-butyl 4-(3-hydroxyphenyl)-3,6-dihydropyridine-1(2H)-carboxylate (5.3 g, 19.2 mmol) was obtained as a combination of two crystallization crops from dichloromethane/hexane crystallization solvents. HRMS m/z 276.1614 (calcd for M+H 276.1594.)

Provenance & Evidence