3,6-Diethoxy-2,5-dihydropyrazine → 3,6-Diethoxy-2-{2-[8-(2-methoxyethoxy)naphthalen-2-ylmethyl]-3-methylbutyl}-2,5-dihydropyrazine

Participants

Reaction Conditions

Reaction Steps

3.03 ml of n-butyllithium (1.6M in hexane) are added dropwise at −40° C. to the suspension of 0.884 g of 3,6-diethoxy-2,5-dihydropyrazine in 12 ml of tetrahydrofuran. After 20 minutes, a solution of 1.265 g of 7-(2-bromomethyl-3-methylbutyl)-1-(2-methoxyethoxy)naphthalene in 5 ml of tetrahydrofuran is added dropwise. The reaction mixture is stirred further at −40″C. for 30 minutes, then warmed to −20° C. over 1 hour. After 18 hours, the reaction mixture is concentrated by evaporation—the residue is partitioned between ethyl acetate and water. The aqueous phase is extracted with ethyl acetate (2×)—the combined organic phases are washed successively with water (2×) and brine, dried over sodium sulphate and concentrated by evaporation. The crude title compound is identified on the basis of the Rf value from the residue.

Provenance & Evidence