4-Chlorobenzaldehyde → HCID 118549276, compound

Participants

Reaction Steps

Following the general procedure, treatment of 4-methylquinoline (0.073 g, 66 μL, 0.50 mmol) and 4-chlorobenzaldehyde (0.105 g, 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=50/50) of the crude reaction mixture afforded 5-(4-chlorophenyl)-8-methyl-5H,6aH-benzo[4,5][1,3]oxazino[3,2-a]quinoline as inseparable mixture of diastereomers as a white solid (0.090 g, 50% yield, dr determined by 1H NMR analysis of crude reaction mixture is 3:1).

Provenance & Evidence