Diethyl Ether → 5-Ethylpentadecan-7-one

참여 물질

반응 단계

A Grignard solution of 2-ethylhexylmagnesiumbromide in diethylether (1.0 M, 110 mL, 0.11 mol) was slowly added via syringe to a stirred mixture of n-octylcyanide (4.66 g, 55 mmol) in diethyl ether (100 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 yellow solid. The resulting solid was purified by recrystallization from acetone to afford white crystals (IX) (4.51 g, 32%). 1H-NMR (CDCl3): δ=2.99-2.79 (m, 4H), 2.64-2.50 (m, 1H), 1.82-1.55 (m, 4H), 1.57-1.03 (m, 18H), 0.89-0.71 (m, 9H). 13C-NMR (CDCl3): δ=164.35, 34.89, 32.44, 30.31, 30.09, 29.90, 29.79, 28.48, 28.31, 25.71, 23.26, 14.71.

출처 및 근거