Hexane → HCID 15007056, compound

Participants

Reaction Steps

4.9 ml of a hexane solution of 8.00 mmols of n-butyl lithium was added to a solution of 968 mg (8.80 mmols) of 1-octyne in 10 ml of tetrahydrofuran in an atmosphere of nitrogen at 0° C. and stirred at the same temperature for 15 minutes. The reaction solution was cooled to -78° C., to which a solution of 10 ml of tetrahydrofuran of 1.83 g (8.00 mmols) of 2-formyl-3-methyl-4-acetoxyquinoline was added, following by heating gradually to room temperature and stirring at room temperature for 1 hour. The reaction solution was poured into 100 ml of water, extracted with ethyl acetate and dried with sodium sulfate. The solvent was distilled off under the reduced pressure and resultant residue was purified by silica gel column chromatography (Wako Gel C-200) (solvent: n-hexane ethyl acetate=2:1) to obtain 1.50 g (yield 55%) of 2-(1 hydroxy-2-nonynyl)-3-methyl-4-acetoxyquinoline.

Provenance & Evidence