Allyl bromide → Ethyl 2-allylhexadecanoate

Participants

Reaction Steps

To a solution of n-butyl lithium (hexane, 0.048 mol) in 120 mL of anhydrous tetrahydrofuran at 0° C. and under argon atmosphere, diisopropylamine was added (6.8 mL, 0.048 mol). Afterwards, ethyl hexadecanoate (11.3 g, 0.04 mol) in tetrahydrofuran (15 mL) was added dropwise and the homogeneous solution was stirred for 1 h at the same temperature. Next, allyl bromide (4.0 mL, 0.048 mol) was added and the resulting mixture was stirred at room temperature for 12 h. The mixture was poured on water, extracted with ethyl acetate, dried over anhydrous sodium sulfate and the solvent evaporated to afford 11.9 g of an oil. The product was chromatographed (silica gel, hexane: ethyl acetate, 3%) to afford 8.7 g of a colorless oil (67% yield).

Provenance & Evidence