Hexane → 5,6,7-Trimethoxy-2-vinylnaphthalene

Participants

Reaction Steps

Methyltriphenylphosphonium bromide (2.8 g) was suspended in dry THF (10 mL) under an argon atmosphere, and a hexane solution (3.3 mL) of 1.7 M tert-butyllithium was added to the suspension at −20° C. After the reaction mixture was warmed to room temperature and stirred for 1 hour, it was cooled again to −20° C., a solution of 5,6,7-trimethoxynaphthalene-2-carboaldehyde (1.26 g) in dry THF (30 mL) was added dropwise thereto, and the mixture was stirred overnight at room temperature. The solvent was distilled off, and water was added to the residue to conduct extraction with ethyl acetate. The resultant organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:8) to obtain the title compound.

Provenance & Evidence