Sodium borohydride → 6-(2-Hydroxyethoxy)-1,2,3,4-tetrahydroquinolin-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)acetate (1.5 g, 6.02 mmol) in ethanol (25 mL), was added calcium chloride (0.334 g, 3.01 mmol). The resulting mixture was cooled to −10° C. and NaBH4 (0.455 g, 12.04 mmol) was added, then stirred at 23° C. for 5 h. The reaction mixture was diluted with EtOAc (50 ml), extracted with sat NaHCO3 solution and brine, dried over anhydrous sodium sulfate, and concentrated to afford a white solid. The crude material was purified by silica gel flash chromatography (12 g, 40-100% ethyl acetate in hexanes) to afford 6-(2-hydroxyethoxy)-3,4-dihydroquinolin-2(1H)-one (0.9 g, 64%) as a white solid. LCMS: RT 0.90 min. LCMS (ES-API), m/z 208.0 (M+H).

Provenance & Evidence