Diethyl Ether → 5,9-Diethyltridecan-7-one

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A Grignard solution of 2-ethylhexylmagnesiumbromide in diethylether (1.0 M, 47 mL, 47 mmol) was slowly added via syringe to a stirred mixture of 3-ethylheptanenitrile (VI) (3.3 g, 24 mmol) in diethyl ether (50 mL) at 0° C. under N2 atmosphere. After stirring for 12 h at reflux temperature, the reaction was quenched with an aqueous HCl-solution (2.0 M, 50 mL) at 0° C. and subsequently vigorously stirred for an additional 3 h at room temperature. The organic phase was separated and the aqueous phase was extracted with diethylether. The combined organic phases were washed with a saturated bicarbonate solution and brine, dried over MgSO4 and evaporated under reduced pressure to give a crude brown oil. The resulting brown oil was purified by vacuum distillation (95° C., 10−2 mbar) to afford a yellow oil (VII). (5.8 g, 35%). 1H-NMR (CDCl3): δ=2.66-2.63 (m, 2H), 2.24 (d, J=6.9 Hz, 4H), 1.36-1.04 (m, 16H), 0.91-0.63 (m, 12H). 13C-NMR (CDCl3): δ=211.59, 48.32, 39.74, 35.53, 33.57, 30.22, 26.65, 23.59, 14.61.

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