Quinoline → HCID 118549306, compound

Participants

Reaction Steps

Following the general procedure, treatment of quinoline (0.064 g, 59 μL, 0.50 mmol) and ethyl 2-oxo-2-phenylacetate (0.134 g, 119 μL, 0.75 mmol) with 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (0.179 g, 146 μL, 0.60 mmol) in the presence of KF (0.070 g, 1.2 mmol) and 18-crown-6 (0.317 g, 1.2 mmol) in THF (2.0 mL) at −10° C. to room temperature for 12 hrs followed by flash column chromatography (Pet. ether/EtOAc=90/10) of the crude reaction mixture afforded ethyl 5-phenyl-5H,6aHbenzo[4,5][1,3]oxazino[3,2-a]quinoline-5-carboxylate as a white solid (0.147 g, 77% yield, dr determined by 1H NMR analysis of crude reaction mixture is >20:1).

Provenance & Evidence