Diisopropylamine → HCID 20314652, compound

Participants

Reaction Steps

To a solution of 56 ml of diisopropylamine in 1200 ml of dry tetrahydrofuran at -78° C was added 260 ml of 1.6 M n-butyllithium in hexane. After 1 hr of stirring 40.4 g of methyl isobutyrate was added dropwise and the solution stirred for another 30 minutes. A 60-g portion of 2,6-bis(bromomethyl)naphthalene was added slowly, and the reaction mixture was stirred overnight and then brought to room temperature. Tetrahydrofuran was removed by evaporation. The residue was dissolved in 300 ml of chloroform, washed 3 times with 400 ml of H2O, dried and evaporated to dryness to obtain 56 g of 2,6-bis(2-carbomethoxy-2-methylpropyl)naphthalene, m.p. 108° C-110° C. The product was recrystallized from benzene.

Provenance & Evidence