N,N,N',N'-Tetramethylethylenediamine → HCID 15204724, compound

Participants

Reaction Steps

To a solution of 3-methoxybenzyl alcohol (50.0 g) in ether (1.1 L) at -20° C. was added n-BuLi (76.0 mL, 10.0M hexanes) at such a rate as to maintain the internal reaction temperature below -10° C. The reaction mixture was then warmed to room temperature, stirred for 2 hours, cooled to 0° C. and tetramethylethylene diamine (42.0 g) was added. The mixture was cooled to -30° C. and then 2-pyridinecarboxaldehyde (58.0 g) was added over 5 minutes. The reaction mixture was warmed to 0° C. quenched with water (500 mL) and then cooled overnight. A precipitate formed which was collected by filtration, washed with ether, and recrystallized from ethanol to afford 30.0 g of α-[2-(hydroxymethyl)-6-methoxyphenyl]-2-pyridinemethanol (Formula XIII: R1 =R7 =H; R2 =6--OCH3).

Provenance & Evidence