Tetrahydrofuran → 6-Methoxy-7-(2-methoxyvinyl)quinoline

Participants

Reaction Steps

While cooling on ice, 0.82 g of potassium t-butoxide was added to 20 ml of a tetrahydrofuran suspension containing 2.50 g of (methoxymethyl)triphenylphosphonium chloride under nitrogen atmosphere. The obtained mixture was then stirred at the same temperature for 10 minutes. Thereafter, 3 ml of a tetrahydrofuran solution containing 545 mg of 6-methoxyquinoline-7-carbaldehyde was added to the reaction solution while cooling on ice, and the obtained mixture was then stirred at the same temperature for 15 minutes. Thereafter, the reaction solution was diluted with ethyl acetate, and then washed with water and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate), so as to obtain 1.41 g of 6-methoxy-7-(2-methoxyvinyl)quinoline containing triphenylphosphine oxide. This compound was used in the next reaction without further purification.

Provenance & Evidence