Hydrochloric Acid → HCID 21973123, compound

Participants

Reaction Steps

At −78° C., 3-ethylenedioxy-1-phenylcyclohexanecarbonitrile (1.66 g, 6.83 mmol) in toluene (20 mL) was added DIBAL-H (1.0 M solution in toluene, 8.88 mL) slowly and was stirred for 1 hr. The reaction mixture was warmed up to room temperature and was added 1N HCl solution (2.60 mL) and was stirred for 1 hr. Saturated sodium bicarbonate was added to quench the reaction and the organic layer was separated. The aqueous layer was extracted with dichloromethane 3 times and the combined organic layers were dried over magnesium sulfate, filtered and concentrated under vacuum. The crude material was purified by filtering through a short silica gel pad with dichloromethane to give the title compound as a white sticky oil (1.43 g, 85% yield). 1H NMR (400 MHz, CDCl3) δ 1.32-1.40 (1H, m), 1.46-1.54 (1H, m), 1.72-1.86 (3H, m), 2.08 (1H, d, J=16 Hz), 2.59-2.67 (2H, m), 3.94-4.07 (4H, m), 7.15-7.36 (5H, m), 9.36 (1H, d, J=4 Hz).

Provenance & Evidence