Ethylene Glycol → HCID 71116097, compound

Participants

Reaction Steps

(S)-3-(nitromethyl)cyclohexanone was synthesized according to the general procedure found in Mei, K.; et al Org. Lett. 2009, 11, 2864-2867. A rt solution containing (3S)-3-(nitromethyl)cyclohexanone (64.6 g, 411 mmol) and ethylene glycol (68.8 mL, 1233 mmol) in THF (741 mL) was treated with HCl (12.5 mL, 411 mmol) under nitrogen. After stirring for 18 h the reaction mixture was concentrated. The residue was dissolved in Et2O and washed with water and saturated aqueous sodium bicarbonate. The combined aqueous layers were washed with Et2O. The combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude residue was purified on two 330 g silica gel columns (0-35% EtOAc/hexanes, 35 min gradient; 100 mL/min elution; 254 nm detection) to provide the title compound (27.7 g, 34% yield) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 4.29 (dd, J=7.03, 11.80 Hz, 2H), 3.94 (d, J=3.01 Hz, 4H), 2.44-2.57 (m, J=3.51, 7.26, 7.26, 11.18, 14.95 Hz, 1H), 1.68-1.83 (m, 4H), 1.54-1.68 (m, 1H), 1.42-1.53 (m, 1H), 1.34 (t, J=12.17 Hz, 1H), 1.09 (ddd, J=3.76, 12.80, 24.59 Hz, 1H). MS (m/z) 202.1 (M+H+).

Provenance & Evidence