1,2-Ethanediamine, N1,N1,N2-trimethyl- → 4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-2-propylbenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.226 g (0.012 mol) of N,N,N'-trimethylethylenediamine in 25 mL of anhydrous THF was added 4.40 mL of a 2.5M solution of n-butyllithium in THF at -20° C. under a nitrogen atmosphere. After 15-20 minutes, 2.501 g (0.010 mol) of the product of Step C dissolved in 5.0 mL of THF was added and the reaction mixture was stirred at -20° C. for an additional 15-20 minutes. Next, 12.0 mL of a 2.5M solution of n-butyllithium in THF was added to the reaction, the cooling bath was removed and the mixture was stirred at room temperature for 3.5 hours. At the end of this period, the reaction mixture was cooled to -40° C. and 5.85 mL of 1-iodopropane was added via syringe. The reaction mixture was then allowed to slowly warm to room temperature and was stirred for 16 hours. The mixture was then partitioned between diethylether and 10% aqueous NaHSO4 and extracted. The organic layer was separated, dried (MgSO4), filtered, and evaporated. The residue was partially purified on a silica gel flash chromatography column eluted with 5% EtOAc-hexane. The semi-purified fractions were combined and evaporated, then rechromatographed on a silica gel flash chromatography column eluted with 50% CHCl3 -hexane. Evaporation of the purified fractions and solvent removal in vacuo afforded 0.386 g (13%) of the title compound.

Provenance & Evidence