N,N,N',N'-Tetramethylethylenediamine → 5-Methyl-1,2,3,4-tetramethoxy-6-(1-hydroxytridec-12-yn-1-yl)benzene

Participants

Reaction Steps

A solution of 5-methyl-1,2,3,4-tetramethoxybenzene (2.12 g, 10 mmol, Hansen, C. A.; Dean, A. B.; Draths, K. M.; Frost, J. W. J. Am. Chem. Soc. 1999, 121(15), 3799-3800.) and tetramethylethylenediamine (TMEDA, 2.96 mL, 20 mmol) in hexanes (25 mL) is cooled at 0° C. in an ice bath while a solution of n-butyllithium (2.0M in hexanes, 5 mL) is added dropwise. The yellow reaction mixture is stirred for thirty minutes and is then diluted with THF (20 mL). A solution of 12-tridecynal (4.27 g, 22 mmol, J. Org. Chem. 2001, 66(14), 4766-4770) in THF (10 mL) is added, and the mixture stirred for two hours. The reaction is quenched by the addition of saturated aqueous NH4Cl (20 mL). Water (30 mL) is added and the aqueous phase is separated and extracted with ethyl acetate (2×50 mL). The combined organic fractions are washed (1× water), dried (saturated aqueous NaCl, sodium sulfate), filtered, and concentrated. Chromatography (hexane-2:1 hexane:ethyl acetate gradient over silica gel 230-400 mesh) provides the desired product.

Provenance & Evidence