反应详情

A Grignard solution of n-octylmagnesiumbromide in diethylether (2.0 M, 100 mL, 0.2 mol) was slowly added via syringe to a stirred mixture of n-octylcyanide (13.92 g, 0.1 mol) 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 an orange solid. The resulting solid was purified recrystallization from methanol to afford yellow crystals (VIII) (18.06 g, 71%). 1H-NMR (CDCl3): δ=2.33 (t, J=7.4 Hz, 4H), 1.58-1.44 (m, 4H), 1.30-1.10 (s, 20H), 0.82 (t, J=6.4 Hz, 6H). 13C-NMR (CDCl3): δ=212.33, 43.42, 32.44, 30.01, 29.90, 29.78, 24.49, 23.26, 14.70.

1. temperatureat reflux temperature
2. customthe reaction was quenched with an aqueous HCl-solution (2.0 M, 50 mL) at 0° C.
3. stirringsubsequently vigorously stirred for an additional 3 h at room temperature
4. customThe organic phase was separated
5. extractionthe aqueous phase was extracted with diethylether
6. washThe combined organic phases were washed with a saturated bicarbonate solution and brine
7. dry with materialdried over MgSO4
8. customevaporated under reduced pressure
9. customto give an orange solid
10. customThe resulting solid was purified
11. customrecrystallization from methanol