Hydrochloric Acid → HCID 15007055, compound

Participants

Reaction Conditions

Reaction Steps

10 ml of a pentane solution of 15.6 mmols of t-butyl lithium was added to 15 ml of 1.86 g (7.8 mmols) of trans-1 -iodo-1-octene ether solution in an atmosphere of argon at -78° C. and stirred at the same temperature for 2 hours. The reaction solution was added to 15 ml of an ether solution of 590 mg (3.10 mmols) of copper iodide at -78° C., after which it was heated up to -35° C. and stirred at the same temperature for 45 minutes. 1.79 g (10 mmols) of hexamethylphosphorus triamide was added to the solution and stirred at -35° C. for 10 minutes, to which 10 ml of a tetrahydrofuran solution of 1.02 g (3.00 mmols) of 2-iodomethyl-3-methyl-4-acetoxyquinoline was added, followed by stirring at the same temperature for 30 minutes. The reaction solution was added to a solution of 3 ml of 1N hydrochloric acid and 100 ml of water, followed by filtration through Celite. The resultant filtrate was extracted with chloroform, washed with water and dried with sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (Wako Gel C-200) (solvent: n-hexane : ethyl acetate=15:1) to obtain 221 mg (yield 23%) of 2-(trans-2-nonenyl)-3-methyl-4-acetoxyquinoline

Provenance & Evidence