Dimethyl Sulfoxide → HCID 19029397, compound

Participants

Reaction Steps

A solution of oxalyl chloride (1.15 mL) in CH2Cl2 (30 mL) was cooled to -78° C. whereupon DMSO (1.87 mL) was added dropwise over 15 mins. This mixture was stirred for 15 minutes. Whereupon a CH2Cl2 (30 mL) solution of 1-[3-(3,4-dichlorophenyl)-5-hydroxy-1-oxopentyl]-1,2,3,4-tetrahydroquinoline (1.0 g) was added over 20 minutes. The mixture was stirred for 30 minutes and then treated with Et3N (7.4 mL) and stirred for an additional 30 minutes at -78° C., followed by 1.5 hours at room temperature. The reaction mixture was quenched with water and diluted with CH2Cl2 (100 mL). The organic fraction was separated, washed sequentially with 1N HCl (1×50 mL), sat. NaHCO3 (1×50 mL) and brine (1×50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to yield an oil. Silica gel chromatography eluting with 5-15% EtOAc/Hex gave the title compound (900 mg).

Provenance & Evidence