Water → HCID 68601375, compound

Participants

Reaction Conditions

Reaction Steps

12.5 ml (31.2 mmol) of n-butyllithium is added dropwise to a solution at −40° C. of 11.1 g (31.2 mmol) of methyl-triphenyl-phosphonium diluted in 100 ml of tetrahydrofuran. The reaction mixture is stirred at 0° C. for 30 minutes and then cooled to −25° C. and a solution of 5 g (20.8 mmol) of 2-methoxy-4-(2-methoxy-ethoxymethoxy)-benzaldehyde diluted in 50 ml of tetrahydrofuran is added dropwise. The reaction mixture is stirred at room temperature for 2 hours. The reaction mixture is treated by adding water and then extracted with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered, and evaporated. The raw product is purified by silica column chromatography, eluted with a heptane/ethyl acetate mixture 75/25 to give 4.4 g (90%) of 2-methoxy-4-(2-methoxy-ethoxymethoxy)-1-vinyl-benzene in the form of a colorless oil.

Provenance & Evidence